Thiophene- or furan-substituted isothiazoline Compounds as Pesticides

ABSTRACT

The present invention relates to thiophene- or furan-substituted isothiazoline compounds of formula I 
     
       
         
         
             
             
         
       
     
     wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

The present invention relates to thiophene- or furan-substitutedisothiazoline compounds which are useful for combating or controllinginvertebrate pests, in particular arthropod pests and nematodes. Theinvention also relates to a method for controlling invertebrate pests byusing these compounds and to plant propagation material and to anagricultural and a veterinary composition comprising said compounds.

Invertebrate pests and in particular arthropods and nematodes destroygrowing and harvested crops and attack wooden dwelling and commercialstructures, causing large economic loss to the food supply and toproperty. While a large number of pesticidal agents are known, due tothe ability of target pests to develop resistance to said agents, thereis an on-going need for new agents for combating invertebrate pests, inparticular insects, arachnids and nematodes.

Related insecticidal aryl isothiazoline compounds are described in WO2013/037626. However, this document does not describe compounds havingthe characteristic substituents and substituents' arrangement as claimedin the present invention. Related insecticidal aryl azoline compoundsare further described in WO 2011/092287, WO 2011/073444, WO 2010/090344,WO 2009/112275 and WO 97/23212. These documents do not describecompounds having the characteristic substituents and substituents'arrangement as claimed in the present invention, either.

It is an object of the present invention to provide compounds that havea good pesticidal activity, in particular insecticidal activity, andshow a broad activity spectrum against a large number of differentinvertebrate pests, especially against difficult to control arthropodpests and/or nematodes.

It has been found that these objectives can be achieved by isothiazolinecompounds of the formula I below, by their stereoisomers and by theirsalts, in particular their agriculturally or veterinarily acceptablesalts.

Therefore, in a first aspect, the invention relates to isothiazolinecompounds of formula I

-   wherein-   X is a heterocyclic radical of formula II

-   wherein-   # is the attachment point to the remainder of the molecule;-   A is a group A¹, A², A³ or A⁴;    -   wherein    -   A¹ is selected from the group consisting of —C(═NR⁶)R⁸,        —S(O)_(n)R⁹, —N(R⁵)R⁶ and —CN;    -   A² is a group of following formula:

-   -   -   wherein        -   # denotes the bond to the aromatic ring of formula (I);        -   W is selected from O and S;        -   Y is selected from hydrogen, —N(R⁵)R⁶ and —OR⁹;

    -   A³ is a group of following formula:

-   -   -   wherein        -   # denotes the bond to the aromatic ring of formula (I);

    -   A⁴ is a 3-, 4-, 5-, 6- or 7-membered saturated, partially        unsaturated or maximally unsaturated heteromonocyclic ring        containing 1, 2, 3 or 4 heteroatoms or heteroatom groups        selected from N, O, S, NO, SO and SO₂, as ring members, or is a        8-, 9- or 10-membered saturated, partially unsaturated or        maximally unsaturated heterobicyclic ring containing 1, 2, 3 or        4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heteromonocyclic or        heterobicyclic ring is optionally substituted with one or more        substituents R¹¹;

-   G is O or S;

-   B¹, B² and B³ are each independently selected from the group    consisting of N and CR², with the proviso that at most two of B¹, B²    and B³ are N;

-   R¹ is selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl and —C(═O)OR¹⁵;

-   each R² is independently selected from the group consisting of    hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅, C₁-C₆-alkyl,    C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the four    last mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more radicals R⁸,    -   —Si(R¹²)₃, —OR⁹, —S(O)_(n)R⁹, —NR^(10a)R^(10b),    -   phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R¹¹,        and a 3-, 4-, 5-, 6-7-, 8-, 9- or 10-membered saturated,        partially unsaturated or maximally unsaturated heteromonocyclic        or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or        heteroatom groups selected from N, O, S, NO, SO and SO₂, as ring        members, where the heteromono- or heterobicyclic ring may be        substituted by one or more radicals R¹¹;

-   R^(3a), R^(3b) are each independently selected from the group    consisting of hydrogen, halogen, hydroxyl, —CO₂R^(3d), C₁-C₃-alkyl,    C₁-C₃-haloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl, C₁-C₃-alkoxy,    C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio,    C₁-C₃-alkylsulfonyl and C₁-C₃-haloalkylsulfonyl; or    -   R^(3a) and R^(3b) together form a group ═O, ═C(R^(3c))₂, ═NOH or        ═NOCH₃;

-   each R^(3c) is independently selected from the group consisting of    hydrogen, halogen, CH₃ and CF₃;

-   R^(3d) is selected from the group consisting of hydrogen,    C₁-C₆-alkyl and C₁-C₃-alkyloxy-C₁-C₃-alkyl-;

-   R^(4a) and R^(4b) are independently selected from the group    consisting of hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅,    C₁-C₆-alkyl which may be partially or fully halogenated and/or may    be substituted by one or more radicals R⁸, C₃-C₈-cycloalkyl which    may be partially or fully halogenated and/or may be substituted by    one or more radicals R⁸, C₂-C₆-alkenyl which may be partially or    fully halogenated and/or may be substituted by one or more radicals    R⁸, C₂-C₆-alkynyl which may be partially or fully halogenated and/or    may be substituted by one or more radicals R⁸,    -   —Si(R¹²)₃, —OR⁹, —S(O)_(n)R⁹, —NR^(10a)R^(10b),    -   phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R¹¹,        and a 3-, 4-, 5-, 6-7-, 8-, 9- or 10-membered saturated,        partially unsaturated or maximally unsaturated heteromonocyclic        or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or        heteroatom groups selected from N, O, S, NO, SO and SO₂, as ring        members, where the heteromonocyclic or heterobicyclic ring may        be substituted by one or more radicals R¹¹;

-   each R⁵ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic and    cycloaliphatic radicals may be partially or fully halogenated and/or    may be substituted with one or more substituents R⁸; and    —S(O)_(n)R⁹,

-   each R⁶ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic and    cycloaliphatic radicals may be partially or fully halogenated and/or    may be substituted by one or more substituents R⁸,    -   —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹,        —C(═O)NR^(10a)N(R^(10a))R^(10b), —Si(R¹²)₃, —C(═O)R⁸, —CH═NOR⁹,    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or        10-membered saturated, partially unsaturated or maximally        unsaturated heteromonocyclic or heterobicyclic ring containing        1, 2, 3 or 4 heteroatoms or heteroatom groups independently        selected from N, O, S, NO, SO and SO₂, as ring members, where        the heteromonocyclic or heterobicyclic ring may be substituted        with one or more substituents R¹¹;    -   or R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, where the ring may further contain 1, 2, 3 or 4        heteroatoms or heteroatom-containing groups selected from O, S,        N, SO, SO₂, C═O and C═S as ring members, wherein the        heterocyclic ring may be substituted with 1, 2, 3, 4 or 5        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, wherein the        aliphatic or cycloaliphatic moieties in the twelve        last-mentioned radicals may be substituted by one or more        radicals R⁸, and phenyl which may be substituted with 1, 2, 3, 4        or 5 substituents R¹¹;    -   or R⁵ and R⁶ together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂,        ═NR^(10a) or ═NOR⁹;

-   R^(7a), R^(7b) are each independently selected from the group    consisting of hydrogen, halogen, cyano, C₁-C₆-alkyl,    C₃-C₈-cycloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl, wherein the four    last-mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more radicals R⁸;

-   each R⁸ is independently selected from the group consisting of    cyano, azido, nitro, —SCN, —SF₅, C₃-C₈-cycloalkyl,    C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkenyl, C₃-C₈-halocycloalkenyl,    where the cycloaliphatic moieties in the four last-mentioned    radicals may be substituted by one or more radicals R¹³;    -   —Si(R¹²)₃, —OR⁹, —OSO₂R⁹, —S(O)_(n)R⁹, —N(R^(10a))R^(10b),        —C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹,        —CH═NOR⁹,    -   phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents        R¹⁶, and    -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated        or maximally unsaturated heterocyclic ring comprising 1, 2 or 3        heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heterocyclic ring is        optionally substituted with one or more substituents R¹⁶, or    -   two R⁸ present on the same carbon atom of an alkyl, alkenyl,        alkynyl or cycloalkyl group together form a group ═O, ═C(R¹³)₂;        ═S; ═S(O)_(m)(R¹⁵)₂,    -   ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR^(10a), ═NOR⁹; or        ═NN(R^(10a))R^(10b);    -   or    -   two radicals R⁸, together with the carbon atoms of an alkyl,        alkenyl, alkynyl or cycloalkyl group which they are bonded to,        form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially        unsaturated carbocyclic or heterocyclic ring, where the        heterocyclic ring comprises 1, 2, 3 or 4 heteroatoms or        heteroatom groups independently selected from N, O, S, NO, SO        and SO₂, as ring members, and where the carbocyclic or        heterocyclic ring is optionally substituted with one or more        substituents R¹⁸; and    -   R⁸ as a substituent on a cycloalkyl ring is additionally        selected from the group consisting of C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl        and C₂-C₆-haloalkynyl, where the aliphatic moieties in these six        radicals may be substituted by one or more radicals R¹³; and    -   R⁸ in the groups —C(═NR⁶)R⁸, —C(═O)R⁸ and ═C(R⁸)₂ is        additionally selected from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl, where        the aliphatic moieties in the six last-mentioned radicals may be        substituted by one or more radicals R¹³;

-   each R⁹ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,    C₃-C₈-cycloalkyl-C₁-C₄-alkyl-, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, where the    aliphatic and cycloaliphatic moieties in the nine last-mentioned    radicals may be substituted by one or more radicals R¹³,    -   —C₁-C₆-alkyl-C(═O)OR¹⁵, —C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), —Si(R¹²)₃, —S(O)_(n)R¹⁵,        —S(O)_(n)N(R^(14a))R^(14b), —N(R^(10a))R^(10b), —N═C(R¹³)₂,        —C(═O)R¹³, —C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b),        —C(═O)OR¹⁵,    -   phenyl, optionally substituted with one or more substituents        R¹⁶; and    -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated        or maximally unsaturated heterocyclic ring comprising 1, 2 or 3        heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heterocyclic ring is        optionally substituted with one or more substituents R¹⁶; and    -   R⁹ in the groups —S(O)_(n)R⁹ and —OSO₂R⁹ is additionally        selected from the group consisting of C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy;

-   R^(10a), R^(10b) are selected independently from one another from    the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, where the    aliphatic and cycloaliphatic moieties in the eight last-mentioned    radicals may be substituted by one or more radicals R¹³;    -   —C₁-C₆-alkyl-C(═O)OR¹⁵, —C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,    -   —S(O)_(n)R¹⁶, —S(O)_(n)N(R^(14a))R^(14b), —C(═O)R¹³, —C(═O)OR¹⁵,        —C(═O)N(R^(14a))R^(14b), —C(═S)R¹³, —C(═S)SR¹⁵,        —C(═S)N(R^(14a))R^(14b), —C(═NR¹⁴)R¹³;    -   phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents        R¹⁶; and    -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated        or maximally unsaturated heterocyclic ring comprising 1, 2, 3 or        4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heterocyclic ring is        optionally substituted with one or more substituents R¹⁶; or    -   R^(10a) and R^(10b) form together with the nitrogen atom they        are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain one        or two heteroatoms or heteroatom groups selected from N, O, S,        NO, SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more substituents selected from        halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl,        optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶,        and a 3-, 4-, 5-, 6, or 7-membered saturated, partially        unsaturated or maximally unsaturated heterocyclic ring        comprising 1, 2 or 3 heteroatoms or heteroatom groups selected        from N, O, S, NO, SO and SO₂, as ring members, where the        heterocyclic ring optionally carries one or more substituents        R¹⁶;    -   or R^(10a), and R^(10b) together form a group ═C(R¹³)₂,        ═S(O)_(m)(R¹⁵)₂, ═S(O)_(m)R¹⁶N(R^(14a))R^(14b), ═NR¹⁴ or ═NOR¹⁵;

-   R¹¹ is independently selected from the group consisting of halogen,    cyano, azido, nitro, —SCN, —SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the four last-mentioned    aliphatic and cycloaliphatic radicals may be partially or fully    halogenated and/or may be substituted with one or more radicals R⁸,    —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹, —Si(R¹²)₃;    -   phenyl, optionally substituted with 1, 2, 3, 4, or 5        substituents selected independently from R¹⁶; and    -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated        or maximally unsaturated aromatic heterocyclic ring comprising        1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N,        O, S, NO, SO and SO₂, as ring members, where the heterocyclic        ring is optionally substituted with one or more substituents        selected independently from R¹⁶;    -   or two R¹¹ present on the same ring carbon atom of an        unsaturated or partially unsaturated heterocyclic ring may        together form a group ═O, ═C(R¹³)₂; ═S; ═S(O)_(m)(R¹⁵)₂;        ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR¹⁴, ═NOR¹⁵, or        ═NN(R^(14a))R^(14b);    -   or two R¹¹ bound on adjacent ring atoms form together with the        ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-,        7-, 8- or 9-membered ring, wherein the ring may contain 1 or 2        heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴,        NO, SO and SO₂ and/or 1 or 2 groups selected from C═O, C═S and        C═NR¹⁴ as ring members, and wherein the ring may be substituted        by one or more radicals selected from the group consisting of        halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl        which may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a        3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or        maximally unsaturated heterocyclic ring containing 1, 2 or 3        heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heterocyclic ring may be        substituted by one or more radicals R¹⁶;

-   each R¹² is independently selected from the group consisting of    hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,    C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,    C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, and phenyl,    optionally substituted with 1, 2, 3, 4, or 5 substituents R¹⁶;

-   each R¹³ is independently selected from the group consisting of    cyano, nitro, —OH, —SH, —SCN, —SF₅, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, —NR^(14a)R^(14b), trimethylsilyl,    triethylsilyl, tert-butyldimethylsilyl, —C(═O)N(R^(14a))R^(14b),    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2 radicals selected from        cyano, C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy and oxo; phenyl, benzyl, phenoxy, where the        phenyl moiety in the three last-mentioned radicals may be        unsubstituted or carry 1, 2, 3, 4 or 5 substituents R¹⁶; and a        3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or        maximally unsaturated heterocyclic ring containing 1, 2 or 3        heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heterocyclic ring may be        substituted by 1, 2 or 3 substituents R¹⁶;    -   or    -   two R¹³ present on the same carbon atom of an alkyl, alkenyl,        alkynyl or cycloalkyl group may together be ═O,        ═CH(C₁-C₄-alkyl), ═C(C₁-C₄-alkyl)C₁-C₄-alkyl, ═NR¹⁷ or ═NOR¹⁷;    -   and    -   R¹³ as a substituent on a cycloalkyl ring is additionally        selected from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl        and C₂-C₆-alkynyl, wherein the three last-mentioned aliphatic        radicals may be unsubstituted, partially or fully halogenated        and/or may carry 1 or 2 substituents selected from CN,        C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo;    -   and    -   R¹³ in the groups ═C(R¹³)₂, —N═C(R¹³)₂, —C(═O)R¹³, —C(═S)R¹³ and        —C(═NR¹⁴)R¹³ is additionally selected from the group consisting        of hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl and        C₂-C₆-alkynyl, wherein the three last-mentioned aliphatic        radicals may be unsubstituted, partially or fully halogenated        and/or may carry 1 or 2 radicals selected from CN,        C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo;

-   each R¹⁴ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,    C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, —C(═O)NR^(18a)R^(18b),    trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three last-mentioned    aliphatic radicals may be unsubstituted, partially or fully    halogenated and/or may carry 1 or 2 radicals selected from CN,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₃-C₆-cycloalkyl which may    be substituted by 1 or 2 substituents selected from halogen and    cyano; and oxo;    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2 radicals selected from        cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyl-C₁-C₄-alkyl-, where the        cycloalkyl moiety in the two last-mentioned radicals may be        substituted by 1 or 2 substituents selected from halogen and        cyano; and oxo;    -   phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties in        the four last-mentioned radicals may be unsubstituted and/or        carry 1, 2, 3 or 4 substituents selected from halogen, cyano,        nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, and        (C₁-C₆-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered        saturated, partially unsaturated or maximally unsaturated        heterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom        groups selected from N, O, S, NO, SO and SO₂, as ring members,        where the heterocyclic ring is optionally substituted with one        or more substituents R¹⁶;

-   R^(14a) and R^(14b), independently of each other, have one of the    meanings given for R¹⁴; or    -   R^(14a) and R^(14b), together with the nitrogen atom to which        they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain 1        or 2 heteroatoms or heteroatom groups selected from N, O, S, NO,        SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more substituents selected from        halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy;    -   or    -   R^(14a) and R¹⁴ or R^(14b) and R¹⁴, together with the nitrogen        atoms to which they are bound in the group        —C(═NR¹⁴)N(R^(14a))R^(14b), form a 3-, 4-, 5-, 6- or 7-membered        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain 1        or 2 heteroatoms or heteroatom groups selected from N, O, S, NO,        SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more substituents selected from        halogen, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

-   each R¹⁵ is independently selected from the group consisting of    hydrogen, cyano, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl,    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three        last-mentioned aliphatic radicals may be unsubstituted,        partially or fully halogenated and/or may carry 1 or 2 radicals        selected from C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl and        oxo; C₃-C₈-cycloalkyl which may be unsubstituted, partially or        fully halogenated and/or may carry 1 or 2 radicals selected from        C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl and        oxo;    -   phenyl, benzyl, pyridyl and phenoxy, wherein the four        last-mentioned radicals may be unsubstituted, partially or fully        halogenated and/or carry 1, 2 or 3 substituents selected from        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and        (C₁-C₆-alkoxy)carbonyl;

-   each R¹⁶ is independently selected from the group consisting of    halogen, nitro, cyano, —OH, —SH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl,    C₁-C₄-haloalkoxycarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl,    di-(C₁-C₄-alkyl)-aminocarbonyl, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl;    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three        last-mentioned aliphatic radicals may be unsubstituted,        partially or fully halogenated and/or may carry 1 or 2 radicals        selected from cyano, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy and oxo;    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2 radicals selected from        cyano, C₁-C₄-alkyl, C₁-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy and oxo;    -   phenyl, benzyl, pyridyl and phenoxy, wherein the four last        mentioned radicals may be unsubstituted, partially or fully        halogenated and/or carry 1, 2 or 3 substituents selected from        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and        (C₁-C₆-alkoxy)carbonyl;    -   or    -   two R¹⁶ present together on the same atom of an unsaturated or        partially unsaturated ring may be ═O, ═S, ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═CH(C₁-C₄-alkyl) or        ═C(C₁-C₄-alkyl)C₁-C₄-alkyl;    -   or    -   two R¹⁶ on two adjacent carbon atoms form together with the        carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered        saturated, partially unsaturated or maximally unsaturated ring,        wherein the ring may contain 1 or 2 heteroatoms or heteroatom        groups selected from N, O, S, NO, SO and SO₂, as ring members,        and wherein the ring optionally carries one or more substituents        selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

-   R¹⁷, R^(18a) and R^(18b), independently of each other and    independently of each occurrence, are selected from the group    consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    wherein the three last-mentioned aliphatic radicals may be    unsubstituted, partially or fully halogenated and/or may carry 1 or    2 radicals selected from CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,    C₁-C₄-cycloalkyl which may be substituted by 1 or 2 substituents    selected from halogen and cyano; and oxo;    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2 radicals selected from        cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl; phenyl and benzyl;

-   each n is independently 0, 1 or 2; and

-   each m is independently 0 or 1;    and the N-oxides, stereoisomers and agriculturally or veterinarily    acceptable salts thereof.

The present invention also provides an agricultural compositioncomprising at least one compound of the formula I as defined hereinand/or an agriculturally acceptable salt thereof and at least one liquidor solid carrier.

The present invention also provides a veterinary composition comprisingat least one compound of the formula I as defined herein and/or aveterinarily acceptable salt thereof and at least one liquid or solidcarrier.

The present invention also provides a method for controllinginvertebrate pests which method comprises treating the pests, their foodsupply, their habitat or their breeding ground or a cultivated plant,plant propagation materials (such as seed), soil, area, material orenvironment in which the pests are growing or may grow, or thematerials, cultivated plants, plant propagation materials (such asseed), soils, surfaces or spaces to be protected from pest attack orinfestation with a pesticidally effective amount of a compound offormula I or a salt thereof as defined herein.

The present invention also relates to plant propagation material, inparticular seed, comprising at least one compound of formula I and/or anagriculturally acceptable salt thereof as defined herein.

The present invention further relates to a method for treating orprotecting an animal from infestation or infection by parasites whichcomprises bringing the animal in contact with a parasiticidallyeffective amount of a compound of the formula I or a veterinarilyacceptable salt thereof as defined herein. Bringing the animal incontact with the compound I, its salt or the veterinary composition ofthe invention means applying or administering it to the animal.

The term “steroisomers” encompasses both optical isomers, such asenantiomers or diastereomers, the latter existing due to more than onecenter of chirality in the molecule, as well as geometrical isomers(cis/trans isomers).

Depending on the substitution pattern, the compounds of the formula Imay have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. One center ofchirality is the carbon ring atom of the isothiazoline ring carryingradical R¹. The invention provides both the pure enantiomers ordiastereomers and their mixtures and the use according to the inventionof the pure enantiomers or diastereomers of the compound I or itsmixtures. Suitable compounds of the formula I also include all possiblegeometrical stereoisomers (cis/trans isomers) and mixtures thereof.

The term N-oxides relates to a form of compounds I in which at least onenitrogen atom is present in oxidized form (as NO). To be more precise,it relates to any compound of the present invention which has at leastone tertiary nitrogen atom that is oxidized to an N-oxide moiety.N-oxides of compounds I can in particular be prepared by e.g. oxidizingthe ring nitrogen atom of the isothiazoline moiety and/or of anynitrogen-containing heterocyclic group present in group A with asuitable oxidizing agent, such as peroxo carboxylic acids or otherperoxides. The person skilled in the art knows if and in which positionscompounds of the present invention may form N-oxides.

The compounds of the present invention may be amorphous or may exist inone ore more different crystalline states (polymorphs) which may have adifferent macroscopic properties such as stability or show differentbiological properties such as activities. The present invention includesboth amorphous and crystalline compounds of the formula I, mixtures ofdifferent crystalline states of the respective compound I, as well asamorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturallyand veterinarily acceptable salts. They can be formed in a customarymethod, e.g. by reacting the compound with an acid of the anion inquestion if the compound of formula I has a basic functionality or byreacting an acidic compound of formula I with a suitable base.

Suitable agriculturally acceptable salts are especially the salts ofthose cations or the acid addition salts of those acids whose cationsand anions, respectively, do not have any adverse effect on the actionof the compounds according to the present invention. Suitable cationsare in particular the ions of the alkali metals, preferably lithium,sodium and potassium, of the alkaline earth metals, preferably calcium,magnesium and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH⁴⁺) andsubstituted ammonium in which one to four of the hydrogen atoms arereplaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl orbenzyl. Examples of substituted ammonium ions comprise methylammonium,isopropylammonium, dimethylammonium, diisopropylammonium,trimethylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium,benzyltrimethylammonium and benzl-triethylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting a compound of formulae I withan acid of the corresponding anion, preferably of hydrochloric acid,hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term “veterinarily acceptable salts” is meant salts of thosecations or anions which are known and accepted in the art for theformation of salts for veterinary use. Suitable acid addition salts,e.g. formed by compounds of formula I containing a basic nitrogen atom,e.g. an amino group, include salts with inorganic acids, for examplehydrochlorids, sulphates, phosphates, and nitrates and salts of organicacids for example acetic acid, maleic acid, dimaleic acid, fumaric acid,difumaric acid, methane sulfenic acid, methane sulfonic acid, andsuccinic acid.

The term “invertebrate pest” as used herein encompasses animalpopulations, such as insects, arachnids and nematodes, which may attackplants, thereby causing substantial damage to the plants attacked, aswell as ectoparasites which may infest animals, in particular warmblooded animals such as e.g. mammals or birds, or other higher animalssuch as reptiles, amphibians or fish, thereby causing substantial damageto the animals infested.

The term “plant propagation material” is to be understood to denote allthe generative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e. g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants,including seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil. The plant propagationmaterials may be treated prophylactically with a plant protectioncompound either at or before planting or transplanting. Said youngplants may also be protected before transplantation by a total orpartial treatment by immersion or pouring.

The term “plants” comprises any types of plants including“non-cultivated plants” and in particular “cultivated plants”.

The term “non-cultivated plants” refers to any wild type species orrelated species or related genera of a cultivated plant.

The term “cultivated plants” is to be understood as including plantswhich have been modified by breeding, mutagenesis or genetic engineeringincluding but not limiting to agricultural biotech products on themarket or in development (cf.http://www.bio.org/speeches/pubs/er/agri_products.asp). Geneticallymodified plants are plants, which genetic material has been so modifiedby the use of recombinant DNA techniques that under naturalcircumstances cannot readily be obtained by cross breeding, mutations ornatural recombination. Typically, one or more genes have been integratedinto the genetic material of a genetically modified plant in order toimprove certain properties of the plant. Such genetic modifications alsoinclude but are not limited to targeted post-translational modificationof protein(s), oligo- or polypeptides e. g. by glycosylation or polymeradditions such as prenylated, acetylated or farnesylated moieties or PEGmoieties.

Plants that have been modified by breeding, mutagenesis or geneticengineering, e. g. have been rendered tolerant to applications ofspecific classes of herbicides, such as auxin herbicides such as dicambaor 2,4-D; bleacher herbicides such as hydroxyl-phenylpyruvatedioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors;acetolactate synthase (ALS) inhibitors such as sulfonyl ureas orimidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS)inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitorssuch as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipidbiosynthesis inhibitors such as acetyl CoA carboxylase (AC-Case)inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as aresult of conventional methods of breeding or genetic engineering.Furthermore, plants have been made resistant to multiple classes ofherbicides through multiple genetic modifications, such as resistance toboth glyphosate and glufosinate or to both glyphosate and a herbicidefrom another class such as ALS inhibitors, HPPD inhibitors, auxinherbicides, or AC-Case inhibitors. These herbicide resistancetechnologies are e. g. described in Pest Managem. Sci. 61, 2005, 246;61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008,326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res.58, 2007, 708; Science 316, 2007, 1185; and references quoted therein.Several cultivated plants have been rendered tolerant to herbicides byconventional methods of breeding (mutagenesis), e. g. Clearfield® summerrape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant tosulfonyl ureas, e. g. tribenuron. Genetic engineering methods have beenused to render cultivated plants such as soybean, cotton, corn, beetsand rape, tolerant to herbicides such as glyphosate and glufosinate,some of which are commercially available under the trade namesRoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance®(imidazolinone tolerant, BASF SE, Germany) and LibertyLink®(glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as δ-endotoxins, e. g. CryIA(b),CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e. g.Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e. g. WO 02/015701). Further examples of such toxins orgenetically modified plants capable of synthesizing such toxins aredisclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451 878, WO 03/18810 and WO 03/52073. The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above. These insecticidal proteins contained in thegenetically modified plants impart to the plants producing theseproteins tolerance to harmful pests from all taxonomic groups ofathropods, especially to beetles (Coeloptera), two-winged insects(Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).Genetically modified plants capable to synthesize one or moreinsecticidal proteins are, e. g., described in the publicationsmentioned above, and some of which are commercially available such asYieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus(corn cultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corncultivars producing the Cry9c toxin), Herculex® RW (corn cultivarsproducing Cry34Ab1, Cry35Ab1 and the enzymePhosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin);Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g.Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe resistance or tolerance of those plants to bacterial, viral orfungal pathogens. Examples of such proteins are the so-called“pathogenesis-related proteins” (PR proteins, see, e. g. EP-A 392 225),plant disease resistance genes (e. g. potato cultivars, which expressresistance genes acting against Phytophthora infestans derived from themexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e. g. bio mass production, grain yield, starchcontent, oil content or protein content), tolerance to drought, salinityor other growth-limiting environmental factors or tolerance to pests andfungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve human or animalnutrition, e. g. oil crops that produce health-promoting long-chainomega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera®rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve raw materialproduction, e. g. potatoes that produce increased amounts of amylopectin(e. g. Amflora® potato, BASF SE, Germany).

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual group members. The prefix C_(n)-C_(m) indicates in eachcase the possible number of carbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine oriodine, in particular fluorine, chlorine or bromine.

The term “alkyl” as used herein and in the alkyl moieties of alkoxy,alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyland the like refers to saturated straight-chain or branched hydrocarbonradicals having 1 to 2 (“C₁-C₂-alkyl”), 1 to 3 (“C₁-C₃-alkyl”), 1 to 4(“C₁-C₄-alkyl”), 1 to 6 (“C₁-C₆-alkyl”), 1 to 8 (“C₁-C₈-alkyl”) or 1 to10 (“C₁- C₁₀-alkyl”) carbon atoms. C₁-C₂-Alkyl is methyl or ethyl.C₁-C₃-Alkyl is additionally propyl and isopropyl. C₁-C₄-Alkyl isadditionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl(isobutyl) or 1,1-dimethylethyl (tert-butyl). C₁-C₆-Alkyl isadditionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or1-ethyl-2-methylpropyl. C₁-C₈-Alkyl is additionally also, for example,heptyl, octyl, 2-ethylhexyl and positional isomers thereof. C₁-C₁₀-Alkylis additionally also, for example, nonyl, decyl and positional isomersthereof.

The term “haloalkyl” as used herein, which is also expressed as “alkylwhich is partially or fully halogenated”, refers to straight-chain orbranched alkyl groups having 1 to 2 (“C₁-C₂-haloalkyl”), 1 to 3(“C₁-C₃-haloalkyl”), 1 to 4 (“C₁-C₄-haloalkyl”), 1 to 6(“C₁-C₆-haloalkyl”), 1 to 8 (“C₁-C₈-haloalkyl”) or 1 to 10(“C₁-C₁₀-haloalkyl”) carbon atoms (as mentioned above), where some orall of the hydrogen atoms in these groups are replaced by halogen atomsas mentioned above: in particular C₁-C₂-haloalkyl, such as chloromethyl,bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.C₁-C₃-haloalkyl is additionally, for example, 1-fluoropropyl,2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl,1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl,heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and thelike. Examples for C₁-C₄-haloalkyl are, apart those mentioned forC₁-C₃-haloalkyl, 4-chlorobutyl and the like.

“Halomethyl” is methyl in which 1, 2 or 3 of the hydrogen atoms arereplaced by halogen atoms. Examples are bromomethyl, chloromethyl,fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl and the like.

The term “alkenyl” as used herein refers to monounsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-alkenyl”), 2 to 4 (“C₂-C₄-alkenyl”), 2 to 6 (“C₂-C₆-alkenyl”), 2to 8 (“C₂-C₈-alkenyl”) or 2 to 10 (“C₂-C₁₀-alkenyl”) carbon atoms and adouble bond in any position, for example C₂-C₃-alkenyl, such as ethenyl,1-propenyl, 2-propenyl or 1-methylethenyl; C₂-C₄-alkenyl, such asethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenylor 2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like,or C₂-C₁₀-alkenyl, such as the radicals mentioned for C₂-C₆-alkenyl andadditionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl,3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl,1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positionalisomers thereof.

The term “haloalkenyl” as used herein, which is also expressed as“alkenyl which is partially or fully halogenated”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-haloalkenyl”), 2 to 4 (“C₂-C₄-haloalkenyl”), 2 to 6(“C₂-C₆-haloalkenyl”), 2 to 8 (“C₂-C₆-haloalkenyl”) or 2 to 10(“C₂-C₁₀-haloalkenyl”) carbon atoms and a double bond in any position(as mentioned above), where some or all of the hydrogen atoms in thesegroups are replaced by halogen atoms as mentioned above, in particularfluorine, chlorine and bromine, for example chlorovinyl, chloroallyl andthe like.

The term “alkynyl” as used herein refers to straight-chain or branchedhydrocarbon groups having 2 to 3 (“C₂-C₃-alkynyl”), 2 to 4(“C₂-C₄-alkynyl”), 2 to 6 (“C₂-C₆-alkynyl”), 2 to 8 (“C₂-C₈-alkynyl”),or 2 to 10 (“C₂-C₁₀-alkynyl”) carbon atoms and one or two triple bondsin any position, for example C₂-C₃-alkynyl, such as ethynyl, 1-propynylor 2-propynyl; C₂-C₄-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl,1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like,C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl,1-ethyl-1-methyl-2-propynyl and the like;

The term “haloalkynyl” as used herein, which is also expressed as“alkynyl which is partially or fully halogenated”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-haloalkynyl”), 2 to 4 (“C₂-C₄-haloalkynyl”), 3 to 4(“C₃-C₄-haloalkynyl”), 2 to 6 (“C₂-C₆-haloalkynyl”), 2 to 8(“C₂-C₈-haloalkynyl”) or 2 to 10 (“C₂-C₁₀-haloalkynyl”) carbon atoms andone or two triple bonds in any position (as mentioned above), where someor all of the hydrogen atoms in these groups are replaced by halogenatoms as mentioned above, in particular fluorine, chlorine and bromine;

The term “cycloalkyl” as used herein refers to mono- or bi- orpolycyclic saturated hydrocarbon radicals having 3 to 8(“C₃-C₈-cycloalkyl”), in particular 3 to 6 (“C₃-C₆-cycloalkyl”) or 3 to5 (“C₃-C₅-cycloalkyl”) or 3 to 4 (“C₃-C₄-cycloalkyl”) carbon atoms.Examples of monocyclic radicals having 3 to 4 carbon atoms comprisecyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl.Examples of monocyclic radicals having 3 to 6 carbon atoms comprisecyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples ofmonocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.Examples of bicyclic radicals having 7 or 8 carbon atoms comprisebicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl andbicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes amonocyclic saturated hydrocarbon radical.

The term “halocycloalkyl” as used herein, which is also expressed as“cycloalkyl which is partially or fully halogenated”, refers to mono- orbi- or polycyclic saturated hydrocarbon groups having 3 to 8(“C₂-C₈-halocycloalkyl”) or preferably 3 to 6 (“C₃-C₆-halocycloalkyl”)or 3 to 5 (“C₃-C₅-halocycloalkyl”) or 3 to 4 (“C₃-C₄-halocycloalkyl”)carbon ring members (as mentioned above) in which some or all of thehydrogen atoms are replaced by halogen atoms as mentioned above, inparticular fluorine, chlorine and bromine.

The term “cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₈-cycloalkyl group(“C₃-C₈-cycloalkyl-C₁-C₄-alkyl”), preferably a C₃-C₆-cycloalkyl group(“C₃-C₆-cycloalkyl-C₁-C₄-alkyl”), more preferably a C₃-C₄-cycloalkylgroup (“C₃-C₄-cycloalkyl-C₁-C₄-alkyl”) as defined above (preferably amonocyclic cycloalkyl group) which is bound to the remainder of themolecule via a C₁-C₄-alkyl group, as defined above. Examples forC₃-C₄-cycloalkyl-C₁-C₄-alkyl are cyclopropylmethyl, cyclopropylethyl,cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl andcyclobutylpropyl, Examples for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, apart thosementioned for C₃-C₄-cycloalkyl-C₁-C₄-alkyl, are cyclopentylmethyl,cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyland cyclohexylpropyl. Examples for C₃-C₈-cycloalkyl-C₁-C₄-alkyl, apartthose mentioned for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, are cycloheptylmethyl,cycloheptylethyl, cyclooctylmethyl and the like.

The term “C₃-C₆-cycloalkyl-methyl” refers to a C₃-C₆-cycloalkyl groupwhich is bound to the remainder of the molecule via a methyl groupExamples are cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl andcyclohexylmethyl.

The term “C₃-C₈-halocycloalkyl-C₁-C₄-alkyl” refers to aC₃-C₈-halocycloalkyl group as defined above which is bound to theremainder of the molecule via a C₁-C₄-alkyl group, as defined above.

The term “cycloalkenyl” as used herein refers to monocyclic hydrocarbonradicals with at least one C═C double bond in the ring, which ring ishowever not aromatic, the hydrocarbon radicals having 3 to 8(“C₃-C₈-cycloalkyl) carbon atoms. Examples are cyclopropenyl, such ascycloprop-1-enyl and cycloprop-2-yl, cyclobutenyl, such ascyclobut-1-enyl and cyclobut-2-enyl, cyclopentenyl, such ascyclopent-1-enyl, cyclopent-2-enyl and cyclopent-3-enyl,cyclopentadienyl, such as cyclopenta-1,3-dienyl, cyclopenta-1,4-dienyland cyclopenta-2,4-dienyl, cyclohexenyl, such as cyclohex-1-enyl,cyclohex-2-enyl and cyclohex-3-enyl, cyclohexadienyl, such ascyclohexa-1,3-dienyl, cyclohexa-1,4-dienyl, cyclohexa-1,5-dienyl andcyclohexa-2,5-dienyl, cycloheptenyl, cycloheptadienyl, cycloheptatrienylcyclooctenyl, cyclooctadieny, cyclooctatrienyl and cyclooctatetraenyl.

The term “halocycloalkenyl” as used herein refers to monocyclichydrocarbon radicals with at least one C═C double bond in the ring,which ring is however not aromatic, the hydrocarbon radicals having 3 to8 (“C₃-C₈-halocycloalkyl”) carbon atoms, and wherein some or all of thehydrogen atoms are replaced by halogen atoms as mentioned above, inparticular fluorine, chlorine and bromine.

The term “C₁-C₂-alkoxy” is a C₁-C₂-alkyl group, as defined above,attached via an oxygen atom. The term “C₁-C₃-alkoxy” is a C₁-C₃-alkylgroup, as defined above, attached via an oxygen atom. The term“C₁-C₄-alkoxy” is a C₁-C₄-alkyl group, as defined above, attached via anoxygen atom. The term “C₁-C₆-alkoxy” is a C₁-C₆-alkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₁₀-alkoxy” is aC₁-C₁₀-alkyl group, as defined above, attached via an oxygen atom.C₁-C₂-Alkoxy is methoxy or ethoxy. C₁-C₃-Alkoxy is additionally, forexample, n-propoxy and 1-methylethoxy (isopropoxy). C₁-C₄-Alkoxy isadditionally, for example, butoxy, 1-methylpropoxy (sec-butoxy),2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy).C₁-C₆-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy. C₁-C₈-Alkoxy is additionally, for example,heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.C₁-C₁₀-Alkoxy is additionally, for example, nonyloxy, decyloxy andpositional isomers thereof.

The term “C₁-C₂-haloalkoxy” is a C₁-C₂-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₃-haloalkoxy” is aC₁-C₃-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₄-haloalkoxy” is a C₁-C₄-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₆-haloalkoxy” is aC₁-C₆-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₁₀-haloalkoxy” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via an oxygen atom. C₁-C₂-Haloalkoxy is, for example,OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂, OCCl3, chlorofluoromethoxy,dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy or OC₂F₅. C₁-C₃-Haloalkoxy is additionally, forexample, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅,1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy or1-(CH₂Br)-2-bromoethoxy.

C₁-C₄-Haloalkoxy is additionally, for example, 4-fluorobutoxy,4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C₁-C₆-Haloalkoxy isadditionally, for example, 5-fluoropentoxy, 5-chloropentoxy,5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy,6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term “C₁-C₃-alkoxy-C₁-C₃-alkyl” as used herein, refers to astraight-chain or branched alkyl group having 1 to 3 carbon atoms, asdefined above, where one hydrogen atom is replaced by a C₁-C₃-alkoxygroup, as defined above. The term “C₁-C₄-alkoxy-C₁-C₄-alkyl” as usedherein, refers to a straight-chain or branched alkyl group having 1 to 4carbon atoms, as defined above, where one hydrogen atom is replaced by aC₁-C₄-alkoxy group, as defined above. The term“C₁-C₆-alkoxy-C₁-C₆-alkyl” as used herein, refers to a straight-chain orbranched alkyl group having 1 to 6 carbon atoms, as defined above, whereone hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above.Examples are methoxymethyl, ethoxymethyl, propoxymethyl,isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl,tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl,1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl,1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl,2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl,2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl,1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl,1-isobutoxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl,2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl,2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl,3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl,3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl,3-tert-butoxypropyl and the like.

The term “C₁-C₄-alkoxy-methyl” as used herein, refers to methyl in whichone hydrogen atom is replaced by a C₁-C₄-alkoxy group, as defined above.The term “C₁-C₆-alkoxy-methyl” as used herein, refers to methyl in whichone hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above.Examples are methoxymethyl, ethoxymethyl, propoxymethyl,isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl,tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.

C₁-C₆-Haloalkoxy-C₁-C₆-alkyl is a straight-chain or branched alkyl grouphaving from 1 to 6, especially 1 to 4 carbon atoms(═C₁-C₆-haloalkoxy-C₁-C₄-alkyl), wherein one of the hydrogen atoms isreplaced by a C₁-C₆-alkoxy group and wherein at least one, e.g. 1, 2, 3,4 or all of the remaining hydrogen atoms (either in the alkoxy moiety orin the alkyl moiety or in both) are replaced by halogen atoms.C₁-C₄-Haloalkoxy-C₁-C₄-alkyl is a straight-chain or branched alkyl grouphaving from 1 to 4 carbon atoms, wherein one of the hydrogen atoms isreplaced by a C₁-C₄-alkoxy group and wherein at least one, e.g. 1, 2, 3,4 or all of the remaining hydrogen atoms (either in the alkoxy moiety orin the alkyl moiety or in both) are replaced by halogen atoms. Examplesare difluoromethoxymethyl (CHF₂OCH₂), trifluoromethoxymethyl,1-difluoromethoxyethyl, 1-trifluoromethoxyethyl, 2-difluoromethoxyethyl,2-trifluoromethoxyethyl, difluoro-methoxy-methyl (CH₃OCF₂),1,1-difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.

The term “C₁-C₂-alkylthio” is a C₁-C₂-alkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₃-alkylthio” is a C₁-C₃-alkylgroup, as defined above, attached via a sulfur atom. The term“C₁-C₄-alkylthio” is a C₁-C₄-alkyl group, as defined above, attached viaa sulfur atom. The term “C₁-C₆-alkylthio” is a C₁-C₆-alkyl group, asdefined above, attached via a sulfur atom. The term “C₁-C₁₀-alkylthio”is a C₁-C₁₀-alkyl group, as defined above, attached via a sulfur atom.C₁-C₂-Alkylthio is methylthio or ethylthio. C₁-C₃-Alkylthio isadditionally, for example, n-propylthio or 1-methylethylthio(isopropylthio). C₁-C₄-Alkylthio is additionally, for example,butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio(isobutylthio) or 1,1-dimethylethylthio (tert-butylthio).C₁-C₆-Alkylthio is additionally, for example, pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio,1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio,3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.C₁-C₈-Alkylthio is additionally, for example, heptylthio, octylthio,2-ethylhexylthio and positional isomers thereof. C₁-C₁₀-Alkylthio isadditionally, for example, nonylthio, decylthio and positional isomersthereof.

The term “C₁-C₂-haloalkylthio” is a C₁-C₂-haloalkyl group, as definedabove, attached via a sulfur atom. The term “C₁-C₃-haloalkylthio” is aC₁-C₃-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₄-haloalkylthio” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₆-haloalkylthio” is aC₁-C₆-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₁₀-haloalkylthio” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfur atom. C₁-C₂-Haloalkylthio is, for example,SCH₂F, SCHF₂, SCF₃, SCH₂Cl, SCHCl₂, SCCl₃, chlorofluoromethylthio,dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio,2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC₂F₅.C₁-C₃-Haloalkylthio is additionally, for example, 2-fluoropropylthio,3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio,2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, SCH₂—C₂F₅, SCF₂—C₂F₅,1-(CH₂F)-2-fluoroethylthio, 1-(CH₂Cl)-2-chloroethylthio or1-(CH₂Br)-2-bromoethylthio. C₁-C₄-Haloalkylthio is additionally, forexample, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio ornonafluorobutylthio. C₁-C₆-Haloalkylthio is additionally, for example,5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio ordodecafluorohexylthio.

The term “C₁-C₂-alkylsulfinyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₃-alkylsulfinyl” isa C₁-C₃-alkyl group, as defined above, attached via a sulfinyl [S(O)]group. The term “C₁-C₄-alkylsulfinyl” is a C₁-C₄-alkyl group, as definedabove, attached via a sulfinyl [S(O)] group. The term“C₁-C₆-alkylsulfinyl” is a C₁-C₆-alkyl group, as defined above, attachedvia a sulfinyl [S(O)] group. The term “C₁-C₁₀-alkylsulfinyl” is aC₁-C₁₀-alkyl group, as defined above, attached via a sulfinyl [S(O)]group. C₁-C₂-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl.C₁-C₃-Alkylsulfinyl is additionally, for example, n-propylsulfinyl and1-methylethylsulfinyl (isopropylsulfinyl). C₁-C₄-Alkylsulfinyl isadditionally, for example, butylsulfinyl, 1-methylpropylsulfinyl(sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C₁-C₆-Alkylsulfinyl isadditionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.C₁-C₈-Alkylsulfinyl is additionally, for example, heptylsulfinyl,octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof.C₁-C₁₀₋Alkylsulfinyl is additionally, for example, nonylsulfinyl,decylsulfinyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfinyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfinyl [S(O)] group. The term“C₁-C₃-haloalkylsulfinyl” is a C₁-C₃-haloalkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₄-haloalkylsulfinyl”is a C₁-C₄-haloalkyl group, as defined above, attached via a sulfinyl[S(O)] group. The term “C₁-C₆-haloalkylsulfinyl” is a C₁-C₆-haloalkylgroup, as defined above, attached via a sulfinyl [S(O)] group. The term“C₁-C₁₀-haloalkylsulfinyl” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfinyl [S(O)] group. C₁-C₂-Haloalkylsulfinyl is,for example, S(O)CH₂F, S(O)CHF₂, S(O)CF₃, S(O)CH₂Cl, S(O)CHCl₂,S(O)CCl₃, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl,chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl,2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl,2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl,2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl,2,2-dichloro-2-fluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl orS(O)C₂F₅. C₁-C₃-Haloalkylsulfinyl is additionally, for example,2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl,2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,2-chloropropylsulfinyl, 3-chloropropylsulfinyl,2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl,3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,3,3,3-trichloropropylsulfinyl, S(O)CH₂—C₂F₅, S(O)CF₂—C₂F₅,1-(CH₂F)-2-fluoroethylsulfinyl, 1-(CH₂Cl)-2-chloroethylsulfinyl and1-(CH₂Br)-2-bromoethylsulfinyl. C₁-C₄-Haloalkylsulfinyl is additionally,for example, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl,4-bromobutylsulfinyl or nonafluorobutylsulfinyl. C₁-C₆-Haloalkylsulfinylis additionally, for example, 5-fluoropentylsulfinyl,5-chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl,undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl,6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl ordodecafluorohexylsulfinyl.

The term “C₁-C₂-alkylsulfonyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term “C₁-C₃-alkylsulfonyl” isa C₁-C₃-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. The term “C₁-C₄-alkylsulfonyl” is a C₁-C₄-alkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-alkylsulfonyl” is a C₁-C₆-alkyl group, as defined above, attachedvia a sulfonyl [S(O)₂] group. The term “C₁-C₁₀-alkylsulfonyl” is aC₁-C₁₀-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. C₁-C₂-Alkylsulfonyl is methylsulfonyl or ethylsulfonyl.C₁-C₃-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or1-methylethylsulfonyl (isopropylsulfonyl). C₁-C₄-Alkylsulfonyl isadditionally, for example, butylsulfonyl, 1-methylpropylsulfonyl(sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or1,1-dimethylethylsulfonyl (tert-butylsulfonyl). C₁-C₆-Alkylsulfonyl isadditionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.C₁-C₈-Alkylsulfonyl is additionally, for example, heptylsulfonyl,octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.C₁-C₁₀-Alkylsulfonyl is additionally, for example, nonylsulfonyl,decylsulfonyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfonyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₃-haloalkylsulfonyl” is a C₁-C₃-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₄-haloalkylsulfonyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-haloalkylsulfonyl” is a C₁-C₆-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₁-haloalkylsulfonyl” is a C₁-C₁₀-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. C₁-C₂-Haloalkylsulfonyl is, forexample, S(O)₂CH₂F, S(O)₂CHF₂, S(O)₂CF₃, S(O)₂CH₂Cl, S(O)₂CHCl₂,S(O)₂CCl₃, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl,chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl,2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl orS(O)₂C₂F₅. C₁-C₃-Haloalkylsulfonyl is additionally, for example,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2-chloropropylsulfonyl, 3-chloropropylsulfonyl,2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl,3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, S(O)₂CH₂—C₂F₅, S(O)₂CF₂—C₂F₅,1-(CH₂F)-2-fluoroethylsulfonyl, 1-(CH₂Cl)-2-chloroethylsulfonylor1-(CH₂Br)-2-bromoethylsulfonyl. C₁-C₄-Haloalkylsulfonyl is additionally,for example, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl,4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C₁-C₆-Haloalkylsulfonylis additionally, for example, 5-fluoropentylsulfonyl,5-chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl,undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl,6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl ordodecafluorohexylsulfonyl.

The substituent “oxo” replaces a CH₂ group by a C(═O) group.

The term “alkylcarbonyl” is a C₁-C₆-alkyl (“C₁-C₆-alkylcarbonyl”),preferably a C₁-C₄-alkyl (“C₁-C₄-alkylcarbonyl”) group, as definedabove, attached via a carbonyl [C(═O)] group. Examples are acetyl(methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl,isopropylcarbonyl, n-butylcarbonyl and the like.

The term “haloalkylcarbonyl” is a C₁-C₆-haloalkyl(“C₁-C₆-haloalkylcarbonyl”), preferably a C₁-C₄-haloalkyl(“C₁-C₄-haloalkylcarbonyl”) group, as defined above, attached via acarbonyl [C(═O)] group. Examples are trifluoromethylcarbonyl,2,2,2-trifluoroethylcarbonyl and the like.

The term “alkoxycarbonyl” is a C₁-C₆-alkoxy (“C₁-C₆-alkoxycarbonyl”),preferably a C₁-C₄-alkoxy (“C₁-C₄-alkoxycarbonyl”) group, as definedabove, attached via a carbonyl [C(═O)] group. Examples aremethoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl,n-butoxycarbonyl and the like.

The term “haloalkoxycarbonyl” is a C₁-C₆-haloalkoxy(“C₁-C₆-haloalkoxycarbonyl”), preferably a C₁-C₄-haloalkoxy(“C₁-C₄-haloalkoxycarbonyl”) group, as defined above, attached via acarbonyl [C(═O)] group. Examples are trifluoromethoxycarbonyl,2,2,2-trifluoroethoxycarbonyl and the like.

The term “C₁-C₆-alkylamino” is a group —N(H)C₁-C₆-alkyl. Examples aremethylamino, ethylamino, propylamino, isopropylamino, butylamino and thelike.

The term “di-(C₁-C₆-alkyl)amino” is a group —N(C₁-C₆-alkyl)₂. Examplesare dimethylamino, diethylamino, ethylmethylamino, dipropylamino,diisopropylamino, methylpropylamino, methylisopropylamino,ethylpropylamino, ethylisopropylamino, dibutylamino and the like.

The term “aminocarbonyl” is a group —C(O)—NH₂.

The term “C₁-C₆-alkylaminocarbonyl” is a group —C(O)—N(H)C₁-C₆-alkyl.Examples are methylaminocarbonyl, ethylaminocarbonyl,propylaminocarbonyl, isopropylaminocarbonyl, butylaminocarbonyl and thelike.

The term “di-(C₁-C₆-alkyl)aminocarbonyl” is a group—C(O)—N(C₁-C₆-alkyl)₂. Examples are dimethylaminocarbonyl,diethylaminocarbonyl, ethylmethylaminocarbonyl, dipropylaminocarbonyl,diisopropylaminocarbonyl, methylpropylaminocarbonyl,methylisopropylaminocarbonyl, ethylpropylaminocarbonyl,ethylisopropylaminocarbonyl, dibutylaminocarbonyl and the like.

The term “3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partiallyunsaturated or maximally unsaturated heterocyclic ring containing 1, 2or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO,SO and SO₂, as ring members” denotes a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or maximum unsaturated heteromonocyclicring or a 8-, 9- or 10-membered saturated, partially unsaturated ormaximally unsaturated heterobicyclic ring containing 1, 2 or 3 (or 4)heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members.

Unsaturated rings contain at least one C—C and/or C—N and/or N—N doublebond(s). Maximally unsaturated rings contain as many conjugated C—Cand/or C—N and/or N—N double bonds as allowed by the ring size.Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic.The heterocyclic ring may be attached to the remainder of the moleculevia a carbon ring member or via a nitrogen ring member. As a matter ofcourse, the heterocyclic ring contains at least one carbon ring atom. Ifthe ring contains more than one O ring atom, these are not adjacent.

The term “3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturatedor maximum unsaturated heterocyclic ring containing 1, 2 or 3 (or 4)heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members” [wherein “maximum unsaturated” includes also“aromatic”] as used herein denotes monocyclic radicals, the monocyclicradicals being saturated, partially unsaturated or maximum unsaturated(including aromatic). The term “3-, 4-, 5-, 6-, 7- or 8-memberedsaturated, partially unsaturated or maximum unsaturated heterocyclicring containing 1, 2 or 3 (or 4) heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members” [wherein“maximum unsaturated” includes also “aromatic”] as used herein furtheralso encompasses 8-membered heteromonocyclic radicals containing 1, 2 or3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, the monocyclic radicals being saturated,partially unsaturated or maximum unsaturated (including aromatic).Unsaturated rings contain at least one C—C and/or C—N and/or N—N doublebond(s). Maximum unsaturated rings contain as many conjugated C—C and/orC—N and/or N—N double bonds as allowed by the ring size. Maximumunsaturated 5- or 6-membered heterocyclic rings are aromatic. 7- and8-membered rings cannot be aromatic. They are homoaromatic (7-memberedring, 3 double bonds) or have 4 double bonds (8-membered ring). Theheterocyclic ring may be attached to the remainder of the molecule via acarbon ring member or via a nitrogen ring member. As a matter of course,the heterocyclic ring contains at least one carbon ring atom. If thering contains more than one 0 ring atom, these are not adjacent.

Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ringinclude: Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl,azetidinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl,pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl,pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl,imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl,oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl,isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl,thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl,isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl,isothiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl,1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl,1,3-dioxan-5-yl, 1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl,piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl,hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl,hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl,piperazin-2-yl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yland 1,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl,morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl,thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl,1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl,1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl, azepan-1-,-2-, -3- or -4-yl, oxepan-2-, -3-, -4- or -5-yl,hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl,hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl,hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the like.

Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturatedheterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- ortetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- ortetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- ortetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- ortetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl,2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl,2,3,4,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-,-5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6-or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl,tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl,tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.

Examples for a 3-, 4-, 5-, 6- or 7-membered maximally unsaturated(including aromatic) heterocyclic ring are 5- or 6-memberedheteroaromatic rings, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl,4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl,2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl,4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 2-pyridinyl,3-pyridinyl, 4-pyridinyl, 1-oxopyridin-2-yl, 1-oxopyridin-3-yl,1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl,4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl, and also homoaromaticradicals, such as 1H-azepine, 1H-[1,3]-diazepine and 1H-[1,4]-diazepine.

Examples for a 8-, 9- or 10-membered saturated heterobicyclic ringcontaining 1, 2 or 3 (or 4) heteroatoms or heteroatom groups selectedfrom N, O, S, NO, SO and SO₂, as ring members are:

Examples for a 8-, 9- or 10-membered partially unsaturatedheterobicyclic ring containing 1, 2 or 3 (or 4) heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ring membersare:

Examples for a 8-, 9- or 10-membered maximally unsaturatedheterobicyclic ring containing 1, 2 or 3 (or 4) heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ring membersare:

In the above structures # denotes the attachment point to the remainderof the molecule. The attachment point is not restricted to the ring onwhich is shown, but can be on either of the fused rings, and may be on acarbon or on a nitrogen ring atom. If the rings carry one or moresubstituents, these may be bound to carbon and/or to nitrogen ring atoms(if the latter are not part of a double bond).

A saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, wherein the ringmay contain 1 or 2 heteroatoms or heteroatom groups selected from O, S,N, NR¹⁴, NO, SO and SO₂ and/or 1 or 2 groups selected from C═O, C═S andC═NR¹⁴ as ring members is either carbocyclic or heterocyclic. Examplesare, in addition to the saturated heteromonocyclic rings mentionedabove, carbocyclic rings, such as cyclopropyl, cyclopropanonyl,cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cyclohexyl,cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl,cyclooctyl, cyclooctanonyl, furan-2-onyl, pyrrolidine-2-onyl,pyrrolidine-2,5-dionyl, piperidine-2-only, piperidine-2,6-dionyl and thelike.

The remarks made below concerning preferred embodiments of the variablesof the compounds of formula I, especially with respect to theirsubstituents A, A¹, A², A³, A⁴, B¹, B², B³, G, W, X, Y, R¹, R², R^(3a),R^(3b), R^(3c), R^(3d), R^(4a), R^(4b), R⁵, R⁶, R^(7a), R^(7b), R⁸, R⁹,R^(10a), R^(10b), R¹¹, R¹², R¹³, R¹⁴, R^(14a), R^(14b), R¹⁵, R¹⁶, R¹⁷,R^(18a), R^(18b), m and n, the features of the use and method accordingto the invention and of the composition of the invention are valid bothon their own and, in particular, in every possible combination with eachother.

In a preferred embodiment, X is selected from heterocyclic radicals offormulae II.1, II.2 and II.3

wherein# is the attachment point to the remainder of the molecule; andG, A, R^(4a) and R^(4b) have one of the above general meanings, or, inparticular, one of the below preferred meanings.

More preferably, X is the heterocyclic radical of formula II.1.

In a preferred embodiment, G is S.

In particular, X is the heterocyclic radical of formula II.1, in which Gis S.

In one embodiment of the invention, A is A¹.

In one preferred embodiment, A¹ is CN.

In another preferred embodiment, A¹ is selected from —C(═NR⁶)R⁸ and—N(R⁵)R⁶ and is more preferably —C(═NR⁶)R⁸; wherein R⁵, R⁶ and R⁸ haveone of the above general meanings, or, in particular, one of the belowpreferred meanings.

R⁶ as a radical in the group —C(═NR⁶)R⁸ is preferably selected fromhydrogen, cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic andcycloaliphatic radicals each independently may be partially or fullyhalogenated and/or may be substituted with 1, 2, 3, 4, 5 or 6,preferably 1, 2 or 3, in particular 1, substituents R⁸; —OR⁹ and—NR^(10a)R^(10b); wherein R⁸, R⁹, R^(10a) and R^(10b) have one of theabove general meanings, or, in particular, one of the below preferredmeanings.

More preferably, R⁶ in —C(═NR⁶)R⁸ is selected from hydrogen,C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, wherein the two last-mentioned aliphaticand cycloaliphatic radicals each independently may be partially or fullyhalogenated and/or may be substituted with 1, 2 or 3, preferably 1 or 2,in particular 1, substituents R⁸; OR⁹ and NR^(10a)R^(10b); wherein R⁸,R⁹, R^(10a) and R^(10b) have one of the above general meanings, or, inparticular, one of the below preferred meanings.

Even more preferably, R⁶ in —C(═NR⁶)R⁸ is selected from —OR⁹ and—NR^(10a)R^(10b); wherein R⁸, R⁹, R^(10a) and R^(10b) have one of theabove general meanings, or, in particular, one of the below preferredmeanings.

In OR⁹ as a preferred meaning of R⁶ in —C(═NR⁶)R⁸, R⁹ is preferablyselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl-, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl, and morepreferably from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl andC₃-C₈-cycloalkyl-C₁-C₄-alkyl-.

In NR^(10a)R^(10b) as a preferred meaning of R⁶ in —C(═NR⁶)R⁸, R^(10a)and R^(10b), independently of each other, are selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,—C(═O)OR¹⁵, —C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), phenylwhich is optionally substituted with 1, 2, 3 or 4 substituents R¹⁶, anda 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring comprising 1, 2, 3 or 4heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, where the heterocyclic ring is optionally substitutedwith one or more substituents R¹⁶;

or R^(10a) and R^(10b) form together with the nitrogen atom they arebonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partiallyunsaturated or maximally unsaturated heterocyclic ring, wherein theheterocyclic ring may additionally contain one or two heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring optionally carries one or moresubstituents selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl;wherein R^(14a), R^(14b), R¹⁵ and R¹⁶ have one of the above generalmeanings, or, in particular, one of the below preferred meanings.

More preferably,

-   R^(10a) is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl;    and-   R^(10b) is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, —C(═O)OR¹⁵,    —C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), phenyl which is    optionally substituted with 1, 2, 3 or 4 substituents R¹⁶, and a 5-    or 6-membered heteroaromatic ring comprising 1, 2 or 3 heteroatoms    selected from N, O and S, as ring members, where the heteroaromatic    ring is optionally substituted with one or more substituents R¹⁶;    -   wherein R^(14a), R^(14b), R¹⁵ and R¹⁶ have one of the above        general meanings, or, in particular, one of the below preferred        meanings.

Even more preferably,

R^(10a) is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; andR^(10b) is selected from —C(═O)N(R^(14a))R^(14b) and—C(═S)N(R^(14a))R^(14b);wherein R^(14a) and R^(14b) have one of the above general meanings, or,in particular, one of the below preferred meanings.

In the above radicals R^(10a) and R^(10b),

-   R^(14a) is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl;    and-   R^(14b) is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₆-alkyl substituted with a CN    group, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, phenyl which is optionally    substituted with 1, 2, 3 or 4 substituents each independently    selected from the group consisting of halogen, cyano, nitro,    C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; and a heterocyclic ring    selected from rings of formulae E-1 to E-54

-   wherein-   k is 0, 1, 2 or 3,-   n is 0, 1 or 2; and-   each R¹⁶ is independently selected from the group consisting of    halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,    C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,    C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,    C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl and    di-(C₁-C₄-alkyl)aminocarbonyl; or    -   two R¹⁶ present on the same carbon atom of a saturated ring may        form together ═O or ═S.

More preferably, in the above radicals R^(10a) and R^(10b),

-   R^(14a) is selected from hydrogen and methyl; and-   R^(14b) is selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-methyl-,    C₃-C₆-cycloalkyl substituted with a CN group, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, phenyl which is optionally substituted with 1, 2,    3 or 4, preferably 1, 2 or 3, in particular 1, substituents R¹⁶    selected from the group consisting of halogen, cyano, nitro,    C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; and a 4-membered saturated    heterocyclic ring comprising one heteroatom or heteroatom group    selected from S, SO and SO₂ as ring member (ring E-44), where the    heterocyclic ring is optionally substituted with one or more,    preferably 1 or 2, in particular 1, substituents R¹⁶;    -   wherein each R¹⁶ is independently selected from the group        consisting of halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or    -   two R¹⁶ present on the same carbon atom may form together a        group ═O or ═S.

Even more preferably, in the above radicals R^(10a) and R^(10b),

-   R¹⁴ is selected from hydrogen and methyl; and-   R^(14b) is selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-methyl-,    C₃-C₆-cycloalkyl substituted with a CN group, C₁-C₆-alkyl    substituted with a CN group, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.

Preferably, in the above radicals, each R¹⁶ is independently selectedfrom halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy.

R⁸ as a radical in the group —C(═NR⁶)R⁸ is preferably selected fromhydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and NR^(10a)R^(10b), and morepreferably from hydrogen and NR^(10a)R^(10b), and is specificallyhydrogen,

wherein R^(10a) and R^(10b) have one of the above general meanings, or,in particular, one of the below preferred meanings.

In this case (i.e. in NR^(10a)R^(10b) as a meaning of R⁸), R^(10a) andR^(10b) are preferably selected, independently of each other, fromhydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,C₁-C₄-alkylaminocarbonyl, C₁-C₄-haloalkylaminocarbonyl,C₃-C₆-cycloalkylaminocarbonyl and C₃-C₆-halocycloalkylaminocarbonyl,

or, together with the nitrogen atom to which they are bound, form a 5-or 6-membered saturated, partially unsaturated or aromatic heterocyclicring, which additionally may contain 1 or 2 further heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring may carry 1 or 2, in particular 1,substituents selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio and C₁-C₄-haloalkylthio.

More preferably, R^(10a) and R^(10b) are in this case selected,independently of each other, from hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₁-C₄-alkylaminocarbonyl and C₁-C₄-haloalkylaminocarbonyl.

In an alternative embodiment of the invention, A is A².

In A², W is preferably O.

In A², Y is preferably N(R⁵)R⁶; wherein R⁵ and R⁶ have one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings.

In an alternatively preferred embodiment, in A² Y is hydrogen.

In an alternatively preferred embodiment, in A² Y is —OR⁹. R⁹ has one ofthe above general meanings, or, in particular, is selected fromhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkyl substituted byone radical R¹³, where R¹³ has one of the above general meanings, or, inparticular, one of the below preferred meanings and is preferablyselected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl and a heterocyclic ringselected from rings of formulae E-1 to E-54 as defined above.

More preferably, in A², W is O and Y is —N(R⁵)R⁶; wherein R⁵ and R⁶ haveone of the above general meanings, or, in particular, one of the belowpreferred meanings.

In alternatively more preferred embodiment, in A², W is O and Y H.

In alternatively more preferred embodiment, in A², W is O and Y is —OR⁹,where R⁹ has one of the above general meanings, or, in particular, isselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkylsubstituted by one radical R¹³, where R¹³ has one of the above generalmeanings, or, in particular, one of the below preferred meaning—sand ispreferably selected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyland a heterocyclic ring selected from rings of formulae E-1 to E-54 asdefined above.

In —N(R⁵)R⁶ as a radical Y,

-   R⁵ is preferably selected from hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,    C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl and C₃-C₈-halocycloalkyl, where    the aforementioned aliphatic and cycloaliphatic radicals may be    substituted by 1, 2 or 3, preferably 1, radicals R⁸; and-   R⁶ is preferably selected from hydrogen, C₁-C₁₀-alkyl,    C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the four    last-mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more, preferably 1, 2 or 3, in particular 1, substituents R⁸,    -   —OR⁹, —NR¹⁰R^(10b), —S(O)_(n)R⁹,        —C(═O)NR^(10a)N(R^(10a)R^(10b)), —C(═O)R⁸, —CH═NOR⁹, phenyl        which may be substituted with 1, 2, 3, 4, or 5, preferably 1, 2        or 3, in particular 1, substituents R¹¹, and    -   a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially        unsaturated or maximally unsaturated heteromonocyclic or        heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or        heteroatom groups independently selected from N, O, S, NO, SO        and SO₂, as ring members, where the heteromonocyclic or        heterobicyclic ring may be substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹¹;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, where the ring may further contain 1, 2, 3 or 4        heteroatoms or heteroatom-containing groups selected from O, S,        SO, SO₂, N, NH, C═O and C═S as ring members, wherein the        heterocyclic ring may be substituted with 1, 2, 3, 4 or 5,        preferably 1, 2 or 3, in particular 1, substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, wherein the        aliphatic or cycloaliphatic moieties in the twelve        last-mentioned radicals may be substituted by one or more,        preferably 1, 2 or 3, in particular 1, radicals R⁸, and phenyl        which may be substituted with 1, 2, 3, 4 or 5, preferably 1, 2        or 3, in particular 1, substituents R¹¹    -   or    -   R⁵ and R⁶ together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂,        ═NR^(10a) or ═NOR⁹;        wherein R⁸, R⁹, R^(10a), R^(10b) and R¹¹ have one of the above        general meanings, or, in particular, one of the below preferred        meanings.

More preferably, in —N(R⁵)R⁶ as a radical Y,

-   R⁵ is selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and    —CH₂—CN; and-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, where the eight    last-mentioned aliphatic and cycloaliphatic radicals may carry 1, 2    or 3 radicals R⁸; C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    —N(R^(10a))R^(10b), —CH═NOR⁹, phenyl which may be substituted with    1, 2, 3, 4, or 5 substituents R¹¹, and a 3-, 4-, 5- or 6-membered    saturated, partially unsaturated or maximally unsaturated    heteromonocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom    groups independently selected from N, O, S, NO, SO and SO₂, as ring    members, where the heteromonocyclic ring may be substituted with one    or more substituents R¹¹;    -   wherein R⁸, R⁹, R^(10a), R^(10b) and R¹¹ have one of the above        general meanings, or, in particular, one of the below preferred        meanings;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5- or 6-membered saturated heterocyclic        ring, where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O as ring members, wherein the heterocyclic ring may be        substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or 3, in        particular 1, substituents independently selected from the group        consisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a group ═S(R⁹)₂, where R⁹ is selected from        C₁-C₆-alkyl and C₁-C₆-haloalkyl.

Even more preferably, in —N(R⁵)R⁶ as a radical Y,

-   R⁵ is selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;    and-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₄-alkyl which carries one radical R⁸, C₂-C₆-alkenyl,    C₂-C₁₀-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be    substituted by 1 or 2 substituents selected from F, CN and pyridyl;    —N(R^(10a))R^(10b), —CH═NOR⁹,    -   phenyl which may be substituted with 1, 2, 3, 4, or 5,        preferably 1, 2 or 3, in particular 1, substituents R¹¹, and a        3-, 4-, 5- or 6-membered saturated, partially unsaturated or        maximally unsaturated heteromonocyclic ring containing 1, 2 or 3        heteroatoms or heteroatom groups independently selected from N,        O, S, NO, SO and SO₂, as ring members, where the        heteromonocyclic ring may be substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹¹;    -   wherein R⁸, R⁹, R^(10a), R^(10b) and R¹¹ have one of the above        general meanings, or, in particular, one of the below preferred        meanings;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5- or 6-membered saturated heterocyclic        ring, where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O as ring members, wherein the heterocyclic ring may be        substituted with 1, 2 or 3, in particular 1, substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a group ═S(R⁹)₂, where R⁹ is selected from        C₁-C₆-alkyl and C₁-C₆-haloalkyl.

Particularly preferably, in —N(R⁵)R⁶ as a radical Y,

-   R⁵ selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;    and-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₄-alkyl which carries one radical R⁸, C₂-C₆-alkenyl,    C₂-C₁₀-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be    substituted by 1 or 2 substituents selected from F, CN and pyridyl;    —N(R^(10a))R^(10b),    -   wherein    -   R^(10a) is selected from hydrogen and C₁-C₆-alkyl; and    -   R^(10b) is selected from hydrogen, —C(═O)N(R^(14a))R^(14b),        phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents        R¹⁶, and a heterocyclic ring selected from rings of formulae E-1        to E-54 as defined above;    -   —CH═NOR⁹, wherein R⁹ is selected from hydrogen, C₁-C₆-alkyl and        C₁-C₆-haloalkyl;    -   phenyl which may be substituted with 1, 2, 3, 4, or 5,        preferably 1, 2 or 3, in particular 1, substituents R¹¹, and    -   a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or        maximally unsaturated heteromonocyclic ring containing 1, 2 or 3        heteroatoms or heteroatom groups independently selected from N,        O, S, NO, SO and SO₂, as ring members, where the        heteromonocyclic ring may be substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹¹;    -   wherein    -   each R¹¹ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₈-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and        C₂-C₄-haloalkynyl; or two R¹¹ present on the same carbon atom of        a saturated heterocyclic ring may form together ═O or ═S;    -   each R⁸ is independently selected from OH, CN, C₃-C₈-cycloalkyl        which optionally carries a CN substituent, C₃-C₈-halocycloalkyl,        C₁-C₈-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl,        C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(10a))R^(10b), phenyl,        optionally substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or        3, in particular 1, substituents R¹⁶, and a 3-, 4-, 5- or        6-membered saturated, partially unsaturated or maximally        unsaturated heteromonocyclic ring containing 1, 2 or 3        heteroatoms or heteroatom groups independently selected from N,        O, S, NO, SO and SO₂, as ring members, where the        heteromonocyclic ring may be substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹⁶;        -   wherein        -   R^(10a) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;        -   R^(10b) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN,            C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,            C₃-C₆-cycloalkylmethyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            phenyl which is optionally substituted with 1, 2, 3, 4 or 5,            preferably 1, 2 or 3, in particular 1, substituents selected            from the group consisting of halogen, cyano, nitro,            C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,            C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,            C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio;            and a heterocyclic ring selected from rings of formulae E-1            to E-54 as defined above; and        -   each R¹⁶ as a substituent on phenyl or the heterocyclic            rings is independently selected from the group consisting of            halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,            C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,            C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and            C₂-C₄-haloalkynyl; or        -   two R¹⁶ present on the same carbon atom of a saturated            heterocyclic ring may form together ═O or ═S;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 5- or 6-membered saturated heterocyclic ring,        where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O as ring members, wherein the heterocyclic ring may be        substituted with 1, 2 or 3, in particular 1, substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy;    -   or    -   R⁵ and R⁶ together form a group ═S(R⁹)₂, where R⁹ is selected        from C₁-C₆-alkyl and C₁-C₆-haloalkyl.

In particular, in N(R⁵)R⁶ as a radical Y,

-   R⁵ is hydrogen or C₁-C₃-alkyl;-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₄-alkyl which carries one radical R⁸, wherein R⁸ is as defined    below; C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituents    selected from F, CN and pyridyl;    -   —N(R^(10a))R^(10b), wherein R^(10a) is selected from hydrogen        and C₁-C₆-alkyl and Rim is selected from hydrogen,        —C(═O)N(R^(14a))R^(14b), wherein R^(14a) is selected from the        group consisting of hydrogen and C₁-C₆-alkyl and R^(14b) is        selected from the group consisting of hydrogen, C₁-C₆-alkyl,        C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; phenyl,        optionally substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or        3, in particular 1, substituents R¹¹, wherein R¹¹ is as defined        below; and a heteroaromatic ring selected from rings of formulae        F-1 to F-54;    -   —CH═NOR⁹, wherein R⁹ is selected from hydrogen, C₁-C₆-alkyl and        C₁-C₆-haloalkyl;    -   phenyl which may be substituted with 1, 2, 3, 4, or 5,        preferably 1, 2 or 3, in particular 1, substituents R¹¹, wherein        R¹¹ is as defined below; and a heteromonocyclic ring selected        from rings of formulae F-1 to F-54

-   -   wherein    -   k is 0, 1, 2 or 3,    -   n is 0, 1 or 2, and    -   each R¹¹ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)-aminocarbonyl; or        -   two R¹¹ present on the same carbon atom of a saturated            heterocyclic ring may form together ═O or ═S;    -   R⁸ is selected from OH, CN, C₃-C₈-cycloalkyl which optionally        carries a CN substituent, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,        —C(═O)N(R^(10a))R^(10b), phenyl, optionally substituted with 1,        2, 3, 4 or 5, preferably 1, 2 or 3, in particular 1,        substituents R¹⁶, and a heterocyclic ring selected from rings of        formulae E-1 to E-54 as defined above;        -   wherein        -   R^(10a) is selected from the group consisting of hydrogen            and C₁-C₆-alkyl;        -   R^(10b) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkynyl,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, CH₂—CN, C₁-C₆-alkoxy            and C₁-C₆-haloalkoxy; and    -   each R¹⁶ as a substituent on phenyl or heterocyclic rings of        formulae E-1 to E-54 is independently selected from the group        consisting of halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)aminocarbonyl; or two R¹⁶ present on the same        carbon atom of a saturated heterocyclic ring may form together        ═O or ═S.

Even more particularly, in —N(R⁵)R⁶ as a radical Y,

-   R⁵ is hydrogen;-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₄-alkyl which carries one radical R⁸, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be    substituted by 1 or 2 substituents selected from F and CN;    -   —N(R^(10a))R^(10b), wherein R^(10a) is hydrogen and R^(10b) is        —C(═O)N(R^(14a))R^(14b), wherein    -   R^(14a) is selected from the group consisting of hydrogen and        C₁-C₆-alkyl; and    -   R^(14b), is selected from the group consisting of hydrogen,        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl, CH₂—CN, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;    -   —CH═NOR⁹, wherein R⁹ is selected from hydrogen, C₁-C₆-alkyl and        C₁-C₆-haloalkyl;    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, and a heteromonocyclic ring selected from        rings of formulae F-1 to F-54 as defined above;    -   wherein    -   R⁸ is selected from CN, C₃-C₈-cycloalkyl which optionally        carries a CN substituent, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,        —C(═O)N(R^(10a))R^(10b), phenyl, optionally substituted with 1,        2, 3, 4 or 5 substituents R¹⁶, and a heterocyclic ring selected        from rings of formulae E-1 to E-54 as defined above; wherein        -   R^(10a) is selected from the group consisting of hydrogen            and C₁-C₆-alkyl;        -   R^(10b) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy, and        -   R¹¹ and R¹⁶; independently of each occurrence and            independently of each other, are selected from the group            consisting of halogen, cyano, nitro, C₁-C₄-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,            C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,            C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,            C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl,            C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,            C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl,            C₁-C₄-haloalkylcarbonyl, aminocarbonyl,            C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl;            or            -   two R¹⁶ present on the same carbon atom of a saturated                heterocyclic ring may form together ═O or ═S.

Specifically, in —N(R⁵)R⁶ as a radical Y,

-   R⁵ is hydrogen;-   R⁶ is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which    carries one radical R⁸, and a heteromonocyclic ring selected from    rings of formulae F-1 to F-54, preferably F-43 to F-49, especially    F-44, as defined above;    -   wherein    -   R⁸ is selected from CN, C₃-C₈-cycloalkyl which optionally        carries a CN substituent, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,        -   —C(═O)N(R^(10a))R^(10b), phenyl, optionally substituted with            1, 2, 3, 4 or 5 substituents R¹⁶, and a heterocyclic ring            selected from rings of formulae E-1 to E-54, preferably E-1            to E-34, especially E-1 to E-3, E-7 and E-26 to E-31, as            defined above; wherein        -   R^(10a) is selected from the group consisting of hydrogen            and C₁-C₆-alkyl;        -   R^(10b) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, and C₁-C₆-haloalkyl, and        -   R¹¹ and R¹⁶; independently of each occurrence and            independently of each other, are selected from the group            consisting of halogen, cyano, nitro, C₁-C₄-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,            C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,            C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,            C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl,            C₃-C₈-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,            C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl,            C₁-C₄-haloalkylcarbonyl, aminocarbonyl,            C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl;            or            -   two R¹⁶ present on the same carbon atom of a saturated                heterocyclic ring may form together ═O or ═S.

In an alternative embodiment of the invention, A is A³.

Preferably, R^(7a) and R^(7b) in the group A³ are independently of eachother selected from hydrogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl,more preferably from hydrogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl. Evenmore preferably, one of R^(7a) and R^(7b) is hydrogen and the other ishydrogen or methyl. Specifically, both are hydrogen.

In the group A³,

-   R⁵ is preferably selected from hydrogen, cyano, C₁-C₆-alkyl,    C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the four    last-mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted with one or    more, preferably 1, 2 or 3, in particular 1, substituents R⁸; and-   R⁶ is preferably selected from hydrogen, C₁-C₆-alkyl,    C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the four    last-mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more, preferably 1, 2 or 3, in particular 1, substituents R⁸,    -   —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹,        —C(═O)NR^(10a)N(R^(10a))R^(10b), —C(═O)R⁸,    -   and a 3-, 4-, 5-, 6- or 7-membered saturated, partially        unsaturated or maximally unsaturated heteromonocyclic or        heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or        heteroatom groups independently selected from N, O, S, NO, SO        and SO₂, as ring members, where the heteromonocyclic or        heterobicyclic ring may be substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹¹;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5- or 6-membered saturated, partially        unsaturated or maximally unsaturated heterocyclic ring, where        the ring may further contain 1, 2, 3 or 4 heteroatoms or        heteroatom-containing groups selected from O, S, N, SO, SO₂, C═O        and C═S as ring members, wherein the heterocyclic ring may be        substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or 3, in        particular 1, substituents independently selected from the group        consisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, wherein the aliphatic or cycloaliphatic        moieties in the twelve last-mentioned radicals may be        substituted by one or more, preferably 1, 2 or 3, in particular        1, radicals R⁸, and phenyl which may be substituted with 1, 2,        3, 4 or 5, preferably 1, 2 or 3, in particular 1, substituents        R¹¹;    -   or    -   R⁵ and R⁶ together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂,        ═NR^(10a) or ═NOR⁹;    -   wherein m, n, R⁸, R⁹, R^(10a), R^(10b) and R¹¹ have one of the        above general meanings, or, in particular, one of the below        preferred meanings.

More preferably, in the group A³,

-   R⁵ is selected from hydrogen, C₁-C₄-alkyl, C₂-C₃-alkynyl, —CH₂—CN    and C₁-C₆-alkoxy-methyl- and preferably from hydrogen and    C₁-C₄-alkyl; and-   R⁶ is —C(═O)R⁸;    wherein R⁸ has one of the above general meanings, or, in particular,    one of the below preferred meanings.

R⁸ in —C(═O)R⁸ as a meaning of the radicals R⁵ and R⁶ of the group A³ ispreferably selected from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, where thealiphatic and cycloaliphatic moieties in the eight last-mentionedradicals may be substituted by one or more, preferably 1, 2 or 3, inparticular 1, radicals R¹³;

—OR⁹, —S(O)_(n)R⁹, —N(R^(10a))R^(10b), —C(═O)N(R^(10a))R^(10b),—CH═NOR⁹,phenyl, optionally substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or3, in particular 1, substituents R¹⁶, and a 3-, 4-, 5- or 6-memberedsaturated, partially unsaturated or maximally unsaturated heterocyclicring comprising 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring isoptionally substituted with one or more, preferably 1, 2 or 3, inparticular 1, substituents R¹⁶,wherein n, R⁹, R^(10a), R^(10b), R¹³ and R¹⁶ have one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings.

More preferably, R⁸ in —C(═O)R⁸ as a meaning of the radicals R⁵ and R⁶of the group A³ is selected from the group consisting of hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkyl substituted with one radicalR¹³, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₃-C₈-cycloalkyl which optionally carries a CN substituent,C₃-C₈-halocycloalkyl,

—N(R^(10a))R^(10b), —C(═O)N(R^(10a))R^(10b), —CH═NOR⁹,phenyl, optionally substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or3, in particular 1, substituents R¹⁶, and a 3-, 4-, 5- or 6-memberedsaturated, partially unsaturated or maximally unsaturated heterocyclicring comprising 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring isoptionally substituted with one or more, preferably 1, 2 or 3, inparticular 1, substituents R¹⁶,wherein R⁹, R^(10a), R^(10b), R¹³ and R¹⁶ have one of the above generalmeanings, or, in particular, one of the below preferred meanings.

R⁹ in —CH═NOR⁹ as a meaning of R⁸ in the group —C(═O)R⁸ as a meaning ofthe radicals R⁵ and R⁶ of the group A³ is preferably selected fromhydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl.

R^(10a) and R^(10b), in —C(═O)N(R^(10a))R^(10b) and —N(R^(10a))R^(10b)as a meaning of R⁸ in the group —C(═O)R⁸ as a meaning of the radicals R⁵and R⁶ of the group A³ are, independently of each other, preferablyselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₃-alkenyl,C₂-C₃-haloalkenyl, C₂-C₃-alkynyl, C₂-C₃-haloalkynyl, C₃-C₆-cycloalkylwhich optionally carries a CN substituent, C₃-C₈-halocycloalkyl, wherethe aliphatic and cycloaliphatic moieties in the 9 last-mentionedradicals may be substituted by one or more radicals R¹³;—C(═O)NR(^(14a))R^(14b), phenyl, optionally substituted with 1, 2, 3, 4or 5 substituents R¹⁶; and a heteromonocyclic ring selected from ringsof formulae E-1 to E-54 as defined above.

R¹³ in R⁸ in the radicals R⁵ and R⁶ of the group A³ is preferablyselected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(14a))R^(14b),phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶;and a heterocyclic ring selected from rings of formulae E-1 to E-54 asdefined above.

R^(14a) and R^(14b) in —C(═O)NR(^(14a))R^(14b) as a meaning for R^(10a)and R^(10b) as well as a meaning for R¹³, independently of each otherand independently of each occurrence, are preferably selected fromhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, wherein the sixlast-mentioned aliphatic radicals may carry 1 substituent selected fromcyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₄-cycloalkyl which may besubstituted by 1 cyano group; and C₃-C₄-halocycloalkyl; C₃-C₈-cycloalkylwhich may carry 1 cyano group; and C₃-C₈-halocycloalkyl; and morepreferably from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, CH₂—CN,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₃-C₆-cycloalkylmethyl-, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

Preferably, each R¹⁶ as a substituent on phenyl or heterocyclic rings offormulae E-1 to E-54 is independently selected from the group consistingof halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)aminocarbonyl; or

two R¹⁶ present on the same carbon atom of a saturated heterocyclic ringmay form together ═O or ═S.

In particular, R⁸ in —C(═O)R⁸ as a meaning of the radicals R⁵ and R⁶ ofthe group A³ is selected from the group consisting of hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl substituted by one radicalR¹³, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₃-C₈-cycloalkyl which optionally carries a CN substituent,C₃-C₈-halocycloalkyl, —N(R^(10a))R^(10b), —C(═O)N(R^(10a))R^(10b),—CH═NOR⁹, phenyl which is optionally substituted with 1, 2, 3, 4 or 5substituents R¹⁶; and a heterocyclic ring selected from rings offormulae E-1 to E-54 as defined above,

wherein

-   R⁹ is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl;-   R^(10a) is selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and    C₃-C₆-cycloalkyl, and preferably from hydrogen and C₁-C₄-alkyl;-   R^(10b) is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₃-C₆-cycloalkyl which optionally carries a CN substituent;    —C(═O)N(R^(14a))R^(14b); phenyl, optionally substituted with 1, 2,    3, 4 or 5 substituents R¹⁶; and a heteromonocyclic ring selected    from rings of formulae E-1 to E-54 as defined above;-   R¹³ is selected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(14a))R^(14b), phenyl, optionally    substituted with 1, 2, 3, 4 or 5 substituents R¹⁶; and a    heterocyclic ring selected from rings of formulae E-1 to E-54 as    defined above;-   R^(14a) is selected from hydrogen and C₁-C₆-alkyl;-   R^(14b) is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    CH₂—CN, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl-, C₁-C₄-alkoxy and    C₁-C₄-haloalkoxy; and    -   each R¹⁶ as a substituent on phenyl or heterocyclic rings of        formulae E-1 to E-54 is independently selected from the group        consisting of halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,        C₁-C₆-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)aminocarbonyl; or two R¹⁶ present on the same        carbon atom of a saturated heterocyclic ring may form together        ═O or ═S.

In an alternative embodiment of the invention, A is A⁴.

A⁴ is preferably selected from a 3-, 4-, 5-, 6- or 7-membered saturated,partially unsaturated or maximally unsaturated heteromonocyclic ringcontaining 1, 2, 3 or 4 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heteromonocyclicring is optionally substituted with one or more, preferably 1, 2 or 3,in particular 1, substituents R¹¹, where R¹¹ has one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings.

More preferably, A⁴ is selected from a 3-, 4-, 5-, 6- or 7-memberedsaturated heteromonocyclic ring containing 1 or 2 heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, a 5-, 6- or 7-membered partially unsaturated heteromonocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, and a 5- or 6-memberedaromatic heteromonocyclic ring containing 1, 2, 3 or 4 heteroatomsselected from N, O and S as ring members, where the heteromonocyclicring is optionally substituted with one or more, preferably 1, 2 or 3,in particular 1, substituents R¹¹, where R¹¹ has one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings.

A⁴ is even more preferably selected from rings of formulae D-1 to D-173

wherein k is 0, 1, 2 or 3, n is 0, 1 or 2 and R¹¹ has one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings;and is in particular selected from D-59, D-65 and D-66 and isspecifically D-59.

Preferably, in the above rings D-1 to D-173,

-   each R¹¹ is independently selected from the group consisting of    halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,    C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,    C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl,    C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or    -   two R¹¹ present on the same carbon atom of a saturated or        partially unsaturated ring may form together ═O or ═S.

Among the radicals A¹, A², A³ and A⁴, preference is given to A².

Preferably, B¹, B² and B³ are CR².

More preferably, B¹ is CR², where R² is not hydrogen, and B² and B³ areCR², where R² has one of the above general meanings or, in particular,one of the below preferred meanings.

Preferably, R² is selected from hydrogen, halogen, cyano, azido, nitro,—SCN, —SF₅, C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,wherein the four last mentioned aliphatic and cycloaliphatic radicalsmay be partially or fully halogenated and/or may be substituted by oneor more radicals R⁸; —OR⁹, —S(O)_(n)R⁹ and —NR^(10a)R^(10b), wherein R⁸,R⁹, R^(10a) and R^(10b) have one of the above general meanings, or, inparticular, one of the below preferred meanings.

More preferably, R² is selected from hydrogen, halogen andC₁-C₂-haloalkyl, preferably from hydrogen, F, Cl, Br and CF₃.

Preferably, R¹ is selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkylC₃-C₆-halocycloalkyl or C(═O)OR¹³; more preferably, from C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and C(═O)OR¹⁵,even more preferably from C₁-C₄-alkyl, C₁-C₄-haloalkyl and —C(═O)OR¹⁵,and particularly preferably from C₁-C₄-haloalkyl and —C(═O)OR¹⁵, whereinR¹⁵ is preferably C₁-C₄-alkyl. In particular, R¹ is C₁-C₄-haloalkyl,specifically C₁-C₂-haloalkyl and more specifically halomethyl, inparticular fluoromethyl, such as fluoromethyl, difluoromethyl andtrifluoromethyl, and is very specifically trifluoromethyl.

Preferably, R^(3a) and R^(3b) are selected, independently of each other,from hydrogen, halogen, hydroxyl, C₁-C₃-alkyl, C₁-C₃-alkenyl,C₁-C₃-alkynyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy, C₁-C₃-alkylthio andC₁-C₃-alkylsulfonyl, more preferably from hydrogen and halogen, inparticular from hydrogen and fluorine and are specifically hydrogen.

Preferably, R^(3a) and R^(3b) are selected, independently of each other,from hydrogen, halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₃-C₅-cycloalkyl, C₃-C₅-halocycloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio. Morepreferably, R^(4a) is hydrogen and R^(4b) is selected from hydrogen,methyl, trifluoromethyl, F, Cl and Br.

If not specified otherwise above, R⁸, R⁹, R^(10a), R^(10b), R¹¹, R¹²,R¹³, R¹⁵ and R¹⁶ have following preferred meanings:

In case R⁸ is a substituent on an alkyl, alkenyl or alkynyl group, it ispreferably selected from the group consisting of cyano,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, —OR⁹, —SR⁹,—C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenylwhich may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-,5-, 6- or 7-membered saturated, partially unsaturated or aromaticheterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring may be substituted by one or more radicals R¹⁶; whereR⁹, R^(10a), R^(10b) and R¹⁶ have one of the meanings given above or inparticular one of the preferred meanings given below.

In case R⁸ is a substituent on an alkyl, alkenyl or alkynyl group, it iseven more preferably selected from the group consisting of cyano,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, —C(═O)N(R^(10a))R^(10b),—C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenyl which may be substituted by1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or aromatic heterocyclic ringcontaining 1, 2 or 3 heteroatoms or heteroatom groups selected from N,O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring maybe substituted by one or more radicals R¹⁶; where R⁹, R^(10a), R^(10b)and R¹⁶ have one of the meanings given above or in particular one of thepreferred meanings given below. In particular it is selected from thegroup consisting of cyano, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,—C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenylwhich may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-,5-, 6- or 7-membered saturated, partially unsaturated or aromaticheterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring may be substituted by one or more radicals R¹⁶; whereR⁹, R^(10a), R^(10b) and R¹⁶ have one of the meanings given above or inparticular one of the preferred meanings given below.

In case R⁸ is a substituent on a cycloalkyl group, it is preferablyselected from the group consisting of cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, —OR⁹, —OSO₂R⁹, —SR⁹,—N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenyl which maybe substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or aromatic heterocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ringmay be substituted by one or more radicals R¹⁶; where R⁹, R^(10a),R^(10b) and R¹⁶ have one of the meanings given above or in particularone of the preferred meanings given below.

In case R⁸ is a substituent on a cycloalkyl group, it is even morepreferably selected from the group consisting of cyano, C₁-C₄-alkyl,C₁-C₃-haloalkyl, C₁-C₄-alkoxy and C₁-C₃-haloalkoxy. In particular, R⁶ asa substituent on a cycloalkyl group is selected from cyano, C₁-C₄-alkyland C₁-C₃-haloalkyl.

In case of R⁸ in a group —C(═O)R⁸, ═C(R⁸)₂ or —C(═NR⁶)R⁸, R⁸ ispreferably selected from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, —OR⁹, —SR⁹, —N(R^(10a))R^(10b), phenyl which may besubstituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or aromatic heterocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ringmay be substituted by one or more radicals R¹⁶; where R⁹, R^(10a),R^(10b) and R¹⁶ have one of the meanings given above or in particularone of the preferred meanings given below.

In case of R⁸ in a group —C(═O)R⁸, ═C(R⁸)₂ or —C(═NR⁶)R⁸, R⁸ is morepreferably selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, —N(R^(10a))R^(10b), phenyl which may be substituted by1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or aromatic heterocyclic ringcontaining 1, 2 or 3 heteroatoms or heteroatom groups selected from N,O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring maybe substituted by one or more radicals R¹⁶; where R^(10a), R^(10b) andR¹⁶ have has one of the meanings given above or in particular one of thepreferred meanings given below.

Preferably, each R⁹ is independently selected from the group consistingof hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl which may besubstituted by 1, 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or aromatic heterocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ringmay be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2,more preferably 1, radicals R¹⁶, where R¹⁶ has one of the meanings givenabove or in particular one of the preferred meanings given below.

More preferably, each R⁹ is independently selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, phenyl which maybe substituted by 1, 2, 3, 4 or 5 radicals R¹⁶; and a 5- or 6-memberedheteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, Oand S, as ring members, where the heteroaromatic ring may be substitutedby one or more radicals R¹⁶; where R¹⁶ has one of the meanings givenabove or in particular one of the preferred meanings given below.

R^(10a) and R^(10b), are, independently of each other, preferablyselected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,C₁-C₄-alkylaminocarbonyl, C₁-C₄-haloalkylaminocarbonyl,C₃-C₆-cycloalkylaminocarbonyl, C₃-C₆-halocycloalkylaminocarbonyl, and a3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatomsor heteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring is optionally substituted with oneor more, preferably 1, 2 or 3, in particular 1, substituents selectedfrom halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthioand C₁-C₄-haloalkylthio;

or, R^(10a) and R^(10b), together with the nitrogen atom to which theyare bound, form a 5- or 6-membered saturated, partially unsaturated oraromatic heterocyclic ring, which additionally may contain 1 or 2further heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, where the heterocyclic ring may carry 1 or 2,in particular 1, substituents selected from halogen, CN, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio.

More preferably, R^(10a) and R^(10b) are, independently of each other,selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ringcomprising 1 heteroatom or heteroatom group selected from N, O, S, NO,SO and SO₂, as ring member, where the heterocyclic ring is optionallysubstituted with one or more, preferably 1, 2 or 3, in particular 1,substituents selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and are specifically, independentlyof each other, selected from hydrogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Each R¹¹ and each R¹⁶ are independently of each occurrence andindependently of each other preferably selected from halogen, CN,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-aralkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl andC₁-C₄-haloalkylsulfonyl, and more preferably from halogen, CN,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

Each R¹² is preferably selected from C₁-C₄-alkyl and is in particularmethyl.

In case R¹³ is a substituent on an alkyl, alkenyl or alkynyl group, itis preferably selected from the group consisting of cyano,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, —OH, —SH, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,C₁-C₄-haloalkylsulfonyl and phenyl which may be substituted by 1, 2 or 3radicals selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

In case R¹³ is a substituent on a cycloalkyl group, it is preferablyselected from the group consisting of cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, —OH, —SH,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,C₁-C₄-haloalkylsulfonyl and phenyl which may be substituted by 1, 2 or 3radicals selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

In case R¹³ is a substituent on a cycloalkyl group, it is even morepreferably selected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₃-haloalkyl, C₁-C₄-alkoxy and C₁-C₃-haloalkoxy. In particular, R¹³as a substituent on a cycloalkyl group is selected from halogen,C₁-C₄-alkyl and C₁-C₃-haloalkyl.

In case of R¹³ in a group —C(═O)R¹³, —C(═S)R¹³, ═C(R¹³)₂ or—C(═NR¹⁴)R¹³, R⁸ is preferably selected from the group consisting ofhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, —OH, —SH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy andphenyl which may be substituted by 1, 2 or 3 radicals selected fromhalogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy.

R¹⁴, R^(14a) and R^(14b) are, independently of each other, preferablyselected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl and benzyl, where the phenyl ring in benzyl isoptionally substituted 1, 2 or 3, in particular 1, substituents selectedfrom halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; or, R^(14a) and R^(14b), together with the nitrogenatom to which they are bound, form a 5- or 6-membered saturated,partially unsaturated or aromatic heterocyclic ring, which additionallymay contain 1 or 2 further heteroatoms or heteroatom groups selectedfrom N, O, S, NO, SO and SO₂, as ring members, where the heterocyclicring may carry 1 or 2, in particular 1, substituents selected fromhalogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy.

More preferably, R¹⁴, R^(14a) and R^(14b) are, independently of eachother, selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and benzyl, where the phenyl ringin benzyl is optionally substituted 1, 2 or 3, in particular 1,substituents selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

or, R^(14a) and R^(14b), together with the nitrogen atom to which theyare bound, form a 5- or 6-membered saturated, partially unsaturated oraromatic heterocyclic ring, which additionally may contain 1 or 2further heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, where the heterocyclic ring may carry 1 or 2,in particular 1, substituents selected from halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

Each R¹⁵ is preferably selected from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the fourlast-mentioned radicals may be unsubstituted and/or carry 1, 2 or 3substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxyand C₁-C₆-haloalkoxy.

In a particular embodiment of the invention, compound I is a compound offormula IA

where A, R^(4a) and R^(4b) have one of the above-given general or, inparticular, one of the above-given preferred meanings, and R^(2a),R^(2b) and R^(2c), independently of each other, have one of the generalor, in particular, one of the preferred meanings given above for R², andwhere R^(4a) is preferably hydrogen.

Examples of preferred compounds are compounds of the following formulaeIa.1 to Ia.37, where R^(2a), R^(2b) and R^(2c) have one of the generalor preferred meanings given above for R² and the other variables haveone of the general or preferred meanings given above. Examples ofpreferred compounds are the individual compounds compiled in the tables1 to 4376 below, Moreover, the meanings mentioned below for theindividual variables in the tables are per se, independently of thecombination in which they are mentioned, a particularly preferredembodiment of the substituents in question.

Table 1

Compounds of the formula Ia.1 in which R^(14b) is hydrogen, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2

Compounds of the formula Ia.1 in which R^(14b) is methyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 3

Compounds of the formula Ia.1 in which R^(14b) is ethyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4

Compounds of the formula Ia.1 in which R^(14b) is propyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 5

Compounds of the formula Ia.1 in which R^(14b) is isopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 6

Compounds of the formula Ia.1 in which R^(14b) is n-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 7

Compounds of the formula Ia.1 in which R^(14b) is sec-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 8

Compounds of the formula Ia.1 in which R^(14b) is isobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 9

Compounds of the formula Ia.1 in which Rub is tert-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 10

Compounds of the formula Ia.1 in which R^(14b) is 2,2-difluoroethyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 11

Compounds of the formula Ia.1 in which R^(14b) is 2,2,2-trifluoroethyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 12

Compounds of the formula Ia.1 in which R^(14b) is 3,3,3-trifluoropropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 13

Compounds of the formula Ia.1 in which R^(14b) is allyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 14

Compounds of the formula Ia.1 in which R^(14b) is propargyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 15

Compounds of the formula Ia.1 in which R^(14b) is cyclopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 16

Compounds of the formula Ia.1 in which R^(14b) is 1-cyanocyclopropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 17

Compounds of the formula Ia.1 in which R^(14b) is cyclobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 18

Compounds of the formula Ia.1 in which R^(14b) is 1-cyanocyclobutyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 19

Compounds of the formula Ia.1 in which R^(14b) is cyclopentyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 20

Compounds of the formula Ia.1 in which R^(14b) is 1-cyanocyclopentyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 21

Compounds of the formula Ia.1 in which R^(14b) is CH₂—CN, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 22

Compounds of the formula Ia.1 in which R^(14b) is CH₂-cyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 23

Compounds of the formula Ia.1 in which R^(14b) isCH₂-(1-cyanocyclopropyl), and the combination of R^(2a), R^(2b), R^(2c)and R^(4b) for a compound corresponds in each case to one row of Table A

Table 24

Compounds of the formula Ia.1 in which R^(14b) is CH₂-cyclobutyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 25

Compounds of the formula Ia.1 in which R^(14b) isCH₂-(1-cyanocyclobutyl), and the combination of R^(2a), R^(2b), R^(2c)and R^(4b) for a compound corresponds in each case to one row of Table A

Table 26

Compounds of the formula Ia.1 in which R^(14b) is CH₂-cyclopentyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 27

Compounds of the formula Ia.1 in which R^(14b) isCH₂-(1-cyanocyclopentyl), and the combination of R^(2a), R^(2b), R^(2c)and R^(4b) for a compound corresponds in each case to one row of Table A

Table 28

Compounds of the formula Ia.1 in which R^(14b) is methoxy, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 29

Compounds of the formula Ia.1 in which R^(14b) is ethoxy, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 30

Compounds of the formula Ia.1 in which R^(14b) is isopropoxy, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Tables 31 to 60

Compounds of the formula Ia.2 in which R^(14b) is as defined in any oftables 1 to 30 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b)for a compound corresponds in each case to one row of Table A

Tables 61 to 90

Compounds of the formula Ia.3 in which R^(14b) is as defined in any oftables 1 to 30 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b)for a compound corresponds in each case to one row of Table A

Tables 91 to 120

Compounds of the formula Ia.4 in which R^(14b) is as defined in any oftables 1 to 30 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b)for a compound corresponds in each case to one row of Table A

Tables 121 to 150

Compounds of the formula Ia.5 in which R^(14b) is as defined in any oftables 1 to 30 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b)for a compound corresponds in each case to one row of Table A

Tables 151 to 180

Compounds of the formula Ia.6 in which R^(14b) is as defined in any oftables 1 to 30 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b)for a compound corresponds in each case to one row of Table A

Tables 181 to 210

Compounds of the formula Ia.7 in which R^(14b) is as defined in any oftables 1 to 30 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b)for a compound corresponds in each case to one row of Table A

Tables 211 to 240

Compounds of the formula Ia.8 in which R^(14b) is as defined in any oftables 1 to 30 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b)for a compound corresponds in each case to one row of Table A

Table 241

Compounds of the formula Ia.9 in which R^(10b) is phenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 242

Compounds of the formula Ia.9 in which R^(10b) is 2-fluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 243

Compounds of the formula Ia.9 in which R^(10b) is 3-fluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 244

Compounds of the formula Ia.9 in which R^(10b) is 4-fluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 245

Compounds of the formula Ia.9 in which R^(10b) is 2-chlorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 246

Compounds of the formula Ia.9 in which R^(10b) is 3-chlorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 247

Compounds of the formula Ia.9 in which R^(4b) is 4-chlorophenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 248

Compounds of the formula Ia.9 in which R^(10b) is 2,3-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 249

Compounds of the formula Ia.9 in which R^(10b) is 2,4-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 250

Compounds of the formula Ia.9 in which R^(10b) is 2,5-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 251

Compounds of the formula Ia.9 in which R^(10b) is 2,6-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 252

Compounds of the formula Ia.9 in which R^(10b) is 3,4-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 253

Compounds of the formula Ia.9 in which R^(10b) is 3,5-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 254

Compounds of the formula Ia.9 in which R^(10b) is 2-methylphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 255

Compounds of the formula Ia.9 in which R^(10b) is 3-methylphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 256

Compounds of the formula Ia.9 in which R^(10b) is 4-methylphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 257

Compounds of the formula Ia.9 in which R^(10b) is 2-methoxyphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 258

Compounds of the formula Ia.9 in which R^(10b) is 3-methoxyphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 259

Compounds of the formula Ia.9 in which R^(10b) is 4-methoxyphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 260

Compounds of the formula Ia.9 in which R^(10b) is pyridin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 261

Compounds of the formula Ia.9 in which R^(10b) is pyridin-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 262

Compounds of the formula Ia.9 in which R^(10b) is pyridin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 263

Compounds of the formula Ia.9 in which R^(10b) is pyrrol-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 264

Compounds of the formula Ia.9 in which R^(10b) is pyrrol-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 265

Compounds of the formula Ia.9 in which R^(10b) is hydrogen, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 266

Compounds of the formula Ia.9 in which R^(10b) is methyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 267

Compounds of the formula Ia.9 in which R^(10b) is ethyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 268

Compounds of the formula Ia.9 in which R^(10b) is propyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 269

Compounds of the formula Ia.9 in which R^(10b) is isopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 270

Compounds of the formula Ia.9 in which R^(10b) is methylcarbonyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 271

Compounds of the formula Ia.9 in which R^(10b) is ethylcarbonyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 272

Compounds of the formula Ia.9 in which R^(10b) is isopropylcarbonyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 273

Compounds of the formula Ia.9 in which R^(10b) is methoxycarbonyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 274

Compounds of the formula Ia.9 in which R^(10b) is ethoxycarbonyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 275

Compounds of the formula Ia.9 in which R^(10b) is isopropoxycarbonyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Tables 276 to 310

Compounds of the formula Ia.10 in which R^(10b) is as defined in tables241 to 275, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) fora compound corresponds in each case to one row of Table A

Tables 311 to 345

Compounds of the formula Ia.11 in which R^(10b) is as defined in tables241 to 275, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) fora compound corresponds in each case to one row of Table A

Tables 346 to 380

Compounds of the formula Ia.12 in which R^(10b) is as defined in tables241 to 275, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) fora compound corresponds in each case to one row of Table A

Table 381

Compounds of the formula Ia.13 in which the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 382

Compounds of the formula Ia.14 in which the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 383

Compounds of the formula Ia.15 in which R⁶ is hydrogen, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 384

Compounds of the formula Ia.15 in which R⁶ is methyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 385

Compounds of the formula Ia.15 in which R⁶ is ethyl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 386

Compounds of the formula Ia.15 in which R⁶ is propyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 387

Compounds of the formula Ia.15 in which R⁶ is isopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 388

Compounds of the formula Ia.15 in which R⁶ is n-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 389

Compounds of the formula Ia.15 in which R⁶ is sec-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 390

Compounds of the formula Ia.15 in which R⁶ is isobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 391

Compounds of the formula Ia.15 in which R⁶ is tert-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 392

Compounds of the formula Ia.15 in which R⁶ is CH₂—C(CH₃)₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 393

Compounds of the formula Ia.15 in which R⁶ is —CH₂CN, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 394

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CH═CH₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 395

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CH₂—CH═CH₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 396

Compounds of the formula Ia.15 in which R⁶ is —CH₂C≡CH, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 397

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂C≡CH, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 398

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂OH, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 399

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂OCH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 400

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂OCH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 401

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂OCH₂CH═CH₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 402

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂OCH₂C≡CH, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 403

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂OCH₂-cyclopropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 404

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂OCF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 405

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂OCH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 406

Compounds of the formula Ia.15 in which R⁶ is —CH(CH₃)CH₂OCH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 407

Compounds of the formula Ia.15 in which R⁶ is —CH(CH₃)CH₂OCH₂CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 408

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂SCH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 409

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂S(O)CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 410

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂S(O)₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 411

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂SCH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 412

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂S(O)CH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 413

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂S(O)₂CH₂CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 414

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂S(O)₂CH₂CH═CH₂, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 415

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂S(O)₂CH₂C≡CH, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 416

Compounds of the formula Ia.15 in which R⁶ is—CH₂CH₂S(O)₂CH₂-cyclopropyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 417

Compounds of the formula Ia.15 in which R⁶ is —CH(CH₃)CH₂SCH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 418

Compounds of the formula Ia.15 in which R⁶ is —CH(CH₃)CH₂S(O)CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 419

Compounds of the formula Ia.15 in which R⁶ is —CH(CH₃)CH₂S(O)₂CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 420

Compounds of the formula Ia.15 in which R⁶ is —C(CH₃)₂CH₂SCH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 421

Compounds of the formula Ia.15 in which R⁶ is —C(CH₃)₂CH₂S(O)CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 422

Compounds of the formula Ia.15 in which R⁶ is —C(CH₃)₂CH₂S(O)₂CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 423

Compounds of the formula Ia.15 in which R⁶ is —CH₂CH₂SCF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 424

Compounds of the formula Ia.15 in which R⁶ is NH₂, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 425

Compounds of the formula Ia.15 in which R⁶ is CH₂CHF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 426

Compounds of the formula Ia.15 in which R⁶ is CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 427

Compounds of the formula Ia.15 in which R⁶ is CH₂CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 428

Compounds of the formula Ia.15 in which R⁶ is CH(CH₃)CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 429

Compounds of the formula Ia.15 in which R⁶ is CH(CF₃)₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 430

Compounds of the formula Ia.15 in which R⁶ is CH₂CH₂CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 431

Compounds of the formula Ia.15 in which R⁶ is CH₂CH═CF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 432

Compounds of the formula Ia.15 in which R⁶ is CH₂CF═CF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 433

Compounds of the formula Ia.15 in which R⁶ is CH₂CH₂CH═CF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 434

Compounds of the formula Ia.15 in which R⁶ is CH₂CH₂CF═CF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 435

Compounds of the formula Ia.15 in which R⁶ is cyclopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 436

Compounds of the formula Ia.15 in which R⁶ is 1-cyano-cyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 437

Compounds of the formula Ia.15 in which R⁶ is1-(pyridin-2-yl)-cyclopropyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 438

Compounds of the formula Ia.15 in which R⁶ is cyclobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 439

Compounds of the formula Ia.15 in which R⁶ is 1-cyano-cyclobutyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 440

Compounds of the formula Ia.15 in which R⁶ is 3,3-difluorocyclobutyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 441

Compounds of the formula Ia.15 in which R⁶ is cyclopentyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 442

Compounds of the formula Ia.15 in which R⁶ is 1-cyano-cyclopentyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 443

Compounds of the formula Ia.15 in which R⁶ is cyclohexyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 444

Compounds of the formula Ia.15 in which R⁶ is 1-cyano-cyclohexyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 445

Compounds of the formula Ia.15 in which R⁶ is —CH₂-cyclopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 446

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-cyano-cyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 447

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-fluoro-cyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 448

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-chloro-cyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 449

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-bromo-cyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 450

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(2,2-difluorocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 451

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(2,2-dichlorocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 452

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(2,2-dibromocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 453

Compounds of the formula Ia.15 in which R⁶ is —CH₂-cyclobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 454

Compounds of the formula Ia.15 in which R⁶ is —CH₂-(1-cyano-cyclobutyl),and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 455

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-fluoro-cyclobutyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 456

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-chloro-cyclobutyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 457

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(2,2-difluorocyclobutyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 458

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(3,3-difluorocyclobutyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 459

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(2,2,3,3-tetrafluorocyclobutyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 460

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(2,2,3,3,4,4-hexafluorocyclobutyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 461

Compounds of the formula Ia.15 in which R⁶ is —CH₂-cyclopentyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 462

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-fluoro-cyclopentyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 463

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-chloro-cyclopentyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 464

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1-cyano-cyclopentyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 465

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(2,2-difluorocyclopentyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 466

Compounds of the formula Ia.15 in which R⁶ is R⁶ is—CH₂-(3,3-difluorocyclopentyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 467

Compounds of the formula Ia.15 in which R⁶ is —CH₂-(1-fluorocyclohexyl),and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 468

Compounds of the formula Ia.15 in which R⁶ is —CH₂-(1-chlorocyclohexyl),and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 469

Compounds of the formula Ia.15 in which R⁶ is —CH₂-(1-cyanocyclohexyl),and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 470

Compounds of the formula Ia.15 in which R⁶ is thietan-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 471

Compounds of the formula Ia.15 in which R⁶ is 1-oxo-thietan-3-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 472

Compounds of the formula Ia.15 in which R⁶ is 1,1-dioxo-thietan-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 473

Compounds of the formula Ia.15 in which R⁶ is 3-methyl-thietan-3-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 474

Compounds of the formula Ia.15 in which R⁶ is3-methyl-1-oxo-thietan-3-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 475

Compounds of the formula Ia.15 in which R⁶ is3-methyl-1,1-dioxo-thietan-3-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 476

Compounds of the formula Ia.15 in which R⁶ is —CH₂-(thietan-3-yl), andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 477

Compounds of the formula Ia.15 in which R⁶ is —CH₂-(1-oxo-thietan-3-yl),and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 478

Compounds of the formula Ia.15 in which R⁶ is—CH₂-(1,1-dioxo-thietan-3-yl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 479

Compounds of the formula Ia.15 in which R⁶ is tetrahydrothiophen-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 480

Compounds of the formula Ia.15 in which R⁶ is1-oxo-tetrahydrothiophen-3-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 481

Compounds of the formula Ia.15 in which R⁶ is1,1-dioxo-tetrahydrothiophen-3-yl, and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 482

Compounds of the formula Ia.15 in which R⁶ is phenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 483

Compounds of the formula Ia.15 in which R⁶ is CH₂—CONH₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 484

Compounds of the formula Ia.15 in which R⁶ is pyridin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 485

Compounds of the formula Ia.15 in which R⁶ is pyridin-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 486

Compounds of the formula Ia.15 in which R⁶ is pyridin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 487

Compounds of the formula Ia.15 in which R⁶ is pyrimidin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 488

Compounds of the formula Ia.15 in which R⁶ is pyrimidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 489

Compounds of the formula Ia.15 in which R⁶ is pyrimidin-5-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 490

Compounds of the formula Ia.15 in which R⁶ is thiazol-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 491

Compounds of the formula Ia.15 in which R⁶ is4-trifluoromethylthiazol-2-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 492

Compounds of the formula Ia.15 in which R⁶ is oxetan-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 493

Compounds of the formula Ia.15 in which R⁶ is tetrahydrofuran-2-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 494

Compounds of the formula Ia.15 in which R⁶ is tetrahydrofuran-3-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 495

Compounds of the formula Ia.15 in which R⁶ is 2-oxotetrahydrofuran-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 496

Compounds of the formula Ia.15 in which R⁶ is 2-oxopyrrolidin-3-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 497

Compounds of the formula Ia.15 in which R⁶ is1-methyl-2-oxopyrrolidin-3-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 498

Compounds of the formula Ia.15 in which R⁶ is2-oxo-1-(2,2,2-trifluoroethyl)-pyrrolidin-3-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 499

Compounds of the formula Ia.15 in which R⁶ is azetidin-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 500

Compounds of the formula Ia.15 in which R⁶ is 1-acetyl-azetidin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 501

Compounds of the formula Ia.15 in which R⁶ is —NH-phenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 502

Compounds of the formula Ia.15 in which R⁶ is —NH-pyridin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 503

Compounds of the formula Ia.15 in which R⁶ is —NH-pyridin-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 504

Compounds of the formula Ia.15 in which R⁶ is —NH-pyridin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 505

Compounds of the formula Ia.15 in which R⁶ is —N(CH₃)-pyridin-2-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 506

Compounds of the formula Ia.15 in which R⁶ is —N(CH₃)-pyrimidin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 507

Compounds of the formula Ia.15 in which R⁶ is —NH-pyrimidin-4-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 508

Compounds of the formula Ia.15 in which R⁶ is —NH-pyrimidin-5-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 509

Compounds of the formula Ia.15 in which R⁶ is —CH₂—C(═O)OCH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 510

Compounds of the formula Ia.15 in which R⁶ is —CH₂—C(═O)O—CH₂CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 511

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 512

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 513

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₂CHF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 514

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 515

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH-cyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 516

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH-isopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 517

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH(CF₃)CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 518

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH(CF₃)₂, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 519

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₂CH₂CF₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 520

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₂CN, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 521

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₂CH═CH₂, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 522

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₂C≡CH, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 523

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CON(CH₃)—CH₂CF₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 524

Compounds of the formula Ia.15 in which R⁶ is —CH(CH₃)—CONH—CH₂CF₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 525

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH—CH₂-cyclopropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 526

Compounds of the formula Ia.15 in which R⁶ is—CH₂—CONH—CH₂-(1-cyano-cyclopropyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 527

Compounds of the formula Ia.15 in which R⁶ is —CH₂—CONH-(thietan-3-yl),and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 528

Compounds of the formula Ia.15 in which R⁶ is—CH₂—CONH-(1-oxo-thietan-3-yl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 529

Compounds of the formula Ia.15 in which R⁶ is—CH₂—CONH-(1,1-dioxo-thietan-3-yl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 530

Compounds of the formula Ia.15 in which R⁶ is benzyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 531

Compounds of the formula Ia.15 in which R⁶ is 2-fluorobenzyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 532

Compounds of the formula Ia.15 in which R⁶ is 3-fluorobenzyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 533

Compounds of the formula Ia.15 in which R⁶ is 4-fluorobenzyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 534

Compounds of the formula Ia.15 in which R⁶ is 2-chlorobenzyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 535

Compounds of the formula Ia.15 in which R⁶ is 3-chlorobenzyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 536

Compounds of the formula Ia.15 in which R⁶ is 4-chlorobenzyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 537

Compounds of the formula Ia.15 in which R⁶ is pyridazin-4-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 538

Compounds of the formula Ia.15 in which R⁶ istetrahydrofuran-2-yl-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 539

Compounds of the formula Ia.15 in which R⁶ is([1,2,3]-thiadiazol-5-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 540

Compounds of the formula Ia.15 in which R⁶ is 2-methylsulfanylbenzyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 541

Compounds of the formula Ia.15 in which R⁶ is 3-methylsulfanylbenzyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 542

Compounds of the formula Ia.15 in which R⁶ is 4-methylsulfanylbenzyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 543

Compounds of the formula Ia.15 in which R⁶ is 2-methylsulfonylbenzyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 544

Compounds of the formula Ia.15 in which R⁶ is 3-methylsulfonylbenzyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 545

Compounds of the formula Ia.15 in which R⁶ is 4-methylsulfonylbenzyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 546

Compounds of the formula Ia.15 in which R⁶ is pyridin-2-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 547

Compounds of the formula Ia.15 in which R⁶ is pyridin-3-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 548

Compounds of the formula Ia.15 in which R⁶ is(6-chloro-pyridin-3-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 549

Compounds of the formula Ia.15 in which R⁶ is pyridin-4-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 550

Compounds of the formula Ia.15 in which R⁶ is(5-chloro-pyridin-2-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 551

Compounds of the formula Ia.15 in which R⁶ is[6-(trifluoromethyl)-pyridin-2-yl]-methyl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 552

Compounds of the formula Ia.15 in which R⁶ is[6-(trifluoromethyl)-pyridin-3-yl]-methyl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 553

Compounds of the formula Ia.15 in which R⁶ is pyrimidin-2-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 554

Compounds of the formula Ia.15 in which R⁶ is pyrimidin-4-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 555

Compounds of the formula Ia.15 in which R⁶ is pyrimidin-5-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 556

Compounds of the formula Ia.15 in which R⁶ is pyridazin-3-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 557

Compounds of the formula Ia.15 in which R⁶ is pyrazin-2-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 558

Compounds of the formula Ia.15 in which R⁶ is thien-2-yl-methyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 559

Compounds of the formula Ia.15 in which R⁶ is thien-3-yl-methyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 560

Compounds of the formula Ia.15 in which R⁶ is thiazol-2-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 561

Compounds of the formula Ia.15 in which R⁶ is thiazol-4-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 562

Compounds of the formula Ia.15 in which R⁶ is thiazol-5-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 563

Compounds of the formula Ia.15 in which R⁶ is(2-chloro-thiazol-5-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 564

Compounds of the formula Ia.15 in which R⁶ is isothiazol-3-yl-methyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 565

Compounds of the formula Ia.15 in which R⁶ is isothiazol-4-yl-methyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 566

Compounds of the formula Ia.15 in which R⁶ is isothiazol-5-yl-methyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 567

Compounds of the formula Ia.15 in which R⁶ is oxazol-2-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 568

Compounds of the formula Ia.15 in which R⁶ is oxazol-4-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 569

Compounds of the formula Ia.15 in which R⁶ is oxazol-5-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 570

Compounds of the formula Ia.15 in which R⁶ is isoxazol-3-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 571

Compounds of the formula Ia.15 in which R⁶ is isoxazol-4-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 572

Compounds of the formula Ia.15 in which R⁶ is isoxazol-5-yl-methyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 573

Compounds of the formula Ia.15 in which R⁶ is([1,2,3]-thiadiazol-4-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 574

Compounds of the formula Ia.15 in which R⁶ is([1,3,4]-thiadiazol-2-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 575

Compounds of the formula Ia.15 in which R⁶ is(1-methyl-imidazol-2-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 576

Compounds of the formula Ia.15 in which R⁶ is(1-methyl-imidazol-4-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 577

Compounds of the formula Ia.15 in which R⁶ is(1-methyl-imidazol-5-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 578

Compounds of the formula Ia.15 in which R⁶ is(1-methyl-pyrazol-3-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 579

Compounds of the formula Ia.15 in which R⁶ is(2-methyl-pyrazol-3-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 580

Compounds of the formula Ia.15 in which R⁶ istetrahydrofuran-3-yl-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 581

Compounds of the formula Ia.15 in which R⁶ is(1,3-dioxolan-2-yl)-methyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 582

Compounds of the formula Ia.15 in which R⁶ is 2-pyridyl-eth-1-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 583

Compounds of the formula Ia.15 in which R⁶ is (1R)-2-pyridyl-eth-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 584

Compounds of the formula Ia.15 in which R⁶ is (1S)-2-pyridyl-eth-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 585

Compounds of the formula Ia.15 in which R⁶ is —CONH₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 586

Compounds of the formula Ia.15 in which R⁶ is —CONN—CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 587

Compounds of the formula Ia.15 in which R⁶ is —CONH—CH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 588

Compounds of the formula Ia.15 in which R⁶ is —CONH—CH₂CH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 589

Compounds of the formula Ia.15 in which R⁶ is —CONH-cyclopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 590

Compounds of the formula Ia.15 in which R⁶ is —CONH—CH₂-cyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 591

Compounds of the formula Ia.15 in which R⁶ is —CONH-phenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 592

Compounds of the formula Ia.15 in which R⁶ is —CONH-benzyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 593

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 594

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 595

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₂CH₂CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 596

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH(CH₃)₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 597

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 598

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₂CHF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 599

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH(CH₃)CF₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 600

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH(CF₃)₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 601

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₂CN, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 602

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₂—CH═CH₂, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 603

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₂—CH═CH, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 604

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH-cyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 605

Compounds of the formula Ia.15 in which R⁶ is—NHCO—NH-(1-cyanocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 606

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH-cyclobutyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 607

Compounds of the formula Ia.15 in which R⁶ is—NHCO—NH-(1-cyanocyclobutyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 608

Compounds of the formula Ia.15 in which R⁶ is —NHCO—NH—CH₂-cyclopropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 609

Compounds of the formula Ia.15 in which R⁶ is—NHCO—NH—CH₂-(1-cyanocyclopropyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 610

Compounds of the formula Ia.15 in which R⁶ is —CH═NOCH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 611

Compounds of the formula Ia.15 in which R⁶ is —CH═NOCH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 612

Compounds of the formula Ia.15 in which R⁶ is 3-oxo-isoxazolidin-4-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 613

Compounds of the formula Ia.15 in which R⁶ is2-methyl-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 614

Compounds of the formula Ia.15 in which R⁶ is2-ethyl-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 615

Compounds of the formula Ia.15 in which R⁶ is2-propyl-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 616

Compounds of the formula Ia.15 in which R⁶ is2-butyl-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 617

Compounds of the formula Ia.15 in which R⁶ is2-(but-2-yl)-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 618

Compounds of the formula Ia.15 in which R⁶ is2-(3-bromopropyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 619

Compounds of the formula Ia.15 in which R⁶ is2-(2-fluoroethyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 620

Compounds of the formula Ia.15 in which R⁶ is2-(2,2-difluoroethyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 621

Compounds of the formula Ia.15 in which R⁶ is2-(2,2,2-trifluoroethyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 622

Compounds of the formula Ia.15 in which R⁶ is2-(3,3,3-trifluoropropyl)-3-oxo-isoxazolidin-4-yl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 623

Compounds of the formula Ia.15 in which R⁶ is2-(2-methoxyethyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 624

Compounds of the formula Ia.15 in which R⁶ is2-(1-methoxy-prop-2-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 625

Compounds of the formula Ia.15 in which R⁶ is2-cyclobutyl-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 626

Compounds of the formula Ia.15 in which R⁶ is2-(2-methylcyclohex-1-yl)-3-oxo-isoxazolidin-4-yl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 627

Compounds of the formula Ia.15 in which R⁶ is2-(phenylmethyl)-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 628

Compounds of the formula Ia.15 in which R⁶ is2-(1-phenyl-eth-1-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 629

Compounds of the formula Ia.15 in which R⁶ is2-(2-phenyl-eth-1-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 630

Compounds of the formula Ia.15 in which R⁶ is2-[(3-chlorophenyl)-methyl]-3-oxo-isoxazolidin-4-yl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 631

Compounds of the formula Ia.15 in which R⁶ is2-[(2-fluorophenyl)-methyl]-3-oxo-isoxazolidin-4-yl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 632

Compounds of the formula Ia.15 in which R⁶ is2-[(4-methoxyphenyl)-methyl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 633

Compounds of the formula Ia.15 in which R⁶ is2-[(2-trifluoromethylphenyl)-methyl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 634

Compounds of the formula Ia.15 in which R⁶ is R⁶ is2-[(2-trifluoromethoxyphenyl)methyl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 635

Compounds of the formula Ia.15 in which R⁶ is2-(pyridin-2-yl-methyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 636

Compounds of the formula Ia.15 in which R⁶ is2-(pyridin-3-yl-methyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 637

Compounds of the formula Ia.15 in which R⁶ is2-[(2-chloropyridin-5-yl)-methyl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 638

Compounds of the formula Ia.15 in which R⁶ is2-[(1-methyl-1H-imidazol-4-yl)-methyl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 639

Compounds of the formula Ia.15 in which R⁶ is2-[(furan-2-yl)-methyl]-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 640

Compounds of the formula Ia.15 in which R⁶ is2-[(2-thiophen-2′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 641

Compounds of the formula Ia.15 in which R⁶ is2-[2-(indol-3′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 642

Compounds of the formula Ia.15 in which R⁶ is2-[(1H-benzimidazol-2-yl)-methyl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 643

Compounds of the formula Ia.15 in which R⁶ is2-[(oxetan-2-yl)-methyl]-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 644

Compounds of the formula Ia.15 in which R⁶ is2-[(tetrahydrofuran-2-yl)-methyl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 645

Compounds of the formula Ia.15 in which R⁶ is2-[(2-[1′,3′]dioxolan-2′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 646

Compounds of the formula Ia.15 in which R⁶ is2-[(2-morpholin-4′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 647

Compounds of the formula Ia.15 in which R⁶ is2-[(2-benzo[1′,3′]dioxol-5′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 648

Compounds of the formula Ia.15 in which R⁶ is2-[(2,3-dihydro-benzo[1,4]dioxin-6-yl)methyl]-3-oxo-isoxazolidin-4-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 649

Compounds of the formula Ia.15 in which R⁶ is2-(2-chlorophenyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 650

Compounds of the formula Ia.15 in which R⁶ is2-(3-fluorophenyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 651

Compounds of the formula Ia.15 in which R⁶ is2-(2-methylphenyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 652

Compounds of the formula Ia.15 in which R⁶ is2-(2-chloro-6-methylphenyl)-3-oxo-isoxazolidin-4-yl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 653

Compounds of the formula Ia.15 in which R⁶ is2-(2-trifluoromethylphenyl)-3-oxo-isoxazolidin-4-yl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 654

Compounds of the formula Ia.15 in which R⁶ is2-(2,4-dimethoxyphenyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 655

Compounds of the formula Ia.15 in which R⁶ is2-(3-methylpyrid-2-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 656

Compounds of the formula Ia.15 in which R⁶ is2-(1,3-dimethyl-1H-pyrazol-5-yl)-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 657

Compounds of the formula Ia.15 in which R⁶ is2-(4-methylthiazol-2-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 658

Compounds of the formula Ia.15 in which R⁶ is2-(5-methylthiadiazol-2-yl)-3-oxo-isoxazolidin-4-yl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 659

Compounds of the formula Ia.15 in which R⁶ is2-(quinolin-2-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 660

Compounds of the formula Ia.15 in which R⁶ is2-(quinolin-5-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 661

Compounds of the formula Ia.15 in which R⁶ is2-(benzothiazol-6-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 662

Compounds of the formula Ia.15 in which R⁶ is2-(4-methylbenzothiazol-2-yl)-3-oxo-isoxazolidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 663

Compounds of the formula Ia.15 in which R⁶ is2-(thietan-3-yl)-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 664

Compounds of the formula Ia.15 in which R⁶ is2-(1-oxo-thietan-3-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 665

Compounds of the formula Ia.15 in which R⁶ is2-(1,1-dioxo-thietan-3-yl)-3-oxo-isoxazolidin-4-yl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 666

Compounds of the formula Ia.15 in which R⁶ is2-(3-methylthietan-3-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 667

Compounds of the formula Ia.15 in which R⁶ is2-(oxetan-3-yl)-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 668

Compounds of the formula Ia.15 in which R⁶ is2-(tetrahydropyran-4-yl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Tables 669 to 954

Compounds of the formula Ia.16 in which R⁶ is as defined in tables 383to 668 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 955 to 1240

Compounds of the formula Ia.17 in which R⁶ is as defined in tables 383to 668 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 1241 to 1526

Compounds of the formula Ia.18 in which R⁶ is as defined in tables 383to 668 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 1527 to 1812

Compounds of the formula Ia.19 in which R⁶ is as defined in tables 383to 668 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 1813 to 2098

Compounds of the formula Ia.20 in which R⁶ is as defined in tables 383to 668 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 2099 to 2384

Compounds of the formula Ia.21 in which R⁶ is as defined in tables 383to 668 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 2385 to 2670

Compounds of the formula Ia.22 in which R⁶ is as defined in tables 383to 668 and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Table 2671

Compounds of the formula Ia.23 in which R^(9a) and R^(9b) are methyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2672

Compounds of the formula Ia.23 in which R^(9a) and R^(9b) are ethyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2673

Compounds of the formula Ia.23 in which R^(9a) and R^(9b) are propyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2674

Compounds of the formula Ia.23 in which R^(9a) and R^(9b) are isopropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2675 to 2678

Compounds of the formula Ia.24 in which R^(9a) and R^(9b) are as definedin tables 2671 to 2674, and the combination of R^(2a), R^(2b), R^(2c)and R^(4b) for a compound corresponds in each case to one row of Table A

Table 2679

Compounds of the formula Ia.25 in which R⁸ is hydrogen, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2680

Compounds of the formula Ia.25 in which R⁸ is methyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2681

Compounds of the formula Ia.25 in which R⁸ is ethyl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2682

Compounds of the formula Ia.25 in which R⁸ is propyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2683

Compounds of the formula Ia.25 in which R⁸ is isopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2684

Compounds of the formula Ia.25 in which R⁸ is n-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2685

Compounds of the formula Ia.25 in which R⁸ is sec-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2686

Compounds of the formula Ia.25 in which R⁸ is isobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2687

Compounds of the formula Ia.25 in which R⁸ is tert-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2688

Compounds of the formula Ia.25 in which R⁸ is CH₂F, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2689

Compounds of the formula Ia.25 in which R⁸ is CHF₂, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2690

Compounds of the formula Ia.25 in which R⁸ is CF₃, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2691

Compounds of the formula Ia.25 in which R⁸ is CH₂CHF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2692

Compounds of the formula Ia.25 in which R⁸ is CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2693

Compounds of the formula Ia.25 in which R⁸ is CF₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2694

Compounds of the formula Ia.25 in which R⁸ is CH₂CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2695

Compounds of the formula Ia.25 in which R⁸ is CH(CH₃)CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2696

Compounds of the formula Ia.25 in which R⁸ is CH(CF₃)₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2697

Compounds of the formula Ia.25 in which R⁸ is CF(CF₃)₂, and thecombination of R^(2a), R^(2b), R^(2b) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2698

Compounds of the formula Ia.25 in which R⁸ is CH₂CN, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2699

Compounds of the formula Ia.25 in which R⁸ is —CH═CH₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2700

Compounds of the formula Ia.25 in which R⁸ is allyl, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2701

Compounds of the formula Ia.25 in which R⁸ is —C≡CH, and the combinationof R^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2702

Compounds of the formula Ia.25 in which R⁸ is propargyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2703

Compounds of the formula Ia.25 in which R⁸ is CN, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2704

Compounds of the formula Ia.25 in which R⁸ is —CH═CHF, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2705

Compounds of the formula Ia.25 in which R⁸ is —CH═CF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2706

Compounds of the formula Ia.25 in which R⁸ is —CF═CF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2707

Compounds of the formula Ia.25 in which R⁸ is cyclopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2708

Compounds of the formula Ia.25 in which R⁸ is 1-fluorocyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2709

Compounds of the formula Ia.25 in which R⁸ is 1-cyanocyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2710

Compounds of the formula Ia.25 in which R⁸ is cyclobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2711

Compounds of the formula Ia.25 in which R⁸ is 1-fluorocyclobutyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2712

Compounds of the formula Ia.25 in which R⁸ is 1-cyanocyclobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2713

Compounds of the formula Ia.25 in which R⁸ is cyclobut-1-enyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2714

Compounds of the formula Ia.25 in which R⁸ is —CH₂-cyclopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2715

Compounds of the formula Ia.25 in which R⁸ is —CH₂-(1-cyanocyclopropyl),and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2716

Compounds of the formula Ia.25 in which R⁸ is —CH₂-cyclobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2717

Compounds of the formula Ia.25 in which R⁸ is —CH₂-(1-cyanocyclobutyl),and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2718

Compounds of the formula Ia.25 in which R⁸ is oxetan-2-yl, and thecombination of R^(2a), R^(2b), R^(2b) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2719

Compounds of the formula Ia.25 in which R⁸ is oxetan-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2720

Compounds of the formula Ia.25 in which R⁸ is tetrahydrofuran-2-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2721

Compounds of the formula Ia.25 in which R⁸ is tetrahydrofuran-3-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2722

Compounds of the formula Ia.25 in which R⁸ is thietan-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2723

Compounds of the formula Ia.25 in which R⁸ is 1-oxo-thietan-3-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2724

Compounds of the formula Ia.25 in which R⁸ is 1,1-dioxo-thietan-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2725

Compounds of the formula Ia.25 in which R⁸ is phenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2726

Compounds of the formula Ia.25 in which R⁸ is 2-fluorophenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2727

Compounds of the formula Ia.25 in which R⁸ is 3-fluorophenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2728

Compounds of the formula Ia.25 in which R⁸ is 4-fluorophenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2729

Compounds of the formula Ia.25 in which R⁸ is 2,3-difluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2730

Compounds of the formula Ia.25 in which R⁸ is 2,4-difluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2731

Compounds of the formula Ia.25 in which R⁸ is 2,5-difluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2732

Compounds of the formula Ia.25 in which R⁸ is 2,6-difluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2733

Compounds of the formula Ia.25 in which R⁸ is 3,4-difluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2734

Compounds of the formula Ia.25 in which R⁸ is 3,5-difluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2735

Compounds of the formula Ia.25 in which R⁸ is 2-chlorophenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2736

Compounds of the formula Ia.25 in which R⁸ is 3-chlorophenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2737

Compounds of the formula Ia.25 in which R⁸ is 4-chlorophenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2738

Compounds of the formula Ia.25 in which R⁸ is 2-methoxyphenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2739

Compounds of the formula Ia.25 in which R⁸ is 3-methoxyphenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2740

Compounds of the formula Ia.25 in which R⁸ is 4-methoxyphenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2741

Compounds of the formula Ia.25 in which R⁸ is pyridin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2742

Compounds of the formula Ia.25 in which R⁸ is pyridin-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2743

Compounds of the formula Ia.25 in which R⁸ is pyridin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2744

Compounds of the formula Ia.25 in which R⁸ is 4-chloropyridin-3-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2745

Compounds of the formula Ia.25 in which R⁸ is pyrimidin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2746

Compounds of the formula Ia.25 in which R⁸ is methoxymethyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2747

Compounds of the formula Ia.25 in which R⁸ is ethoxymethyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2748

Compounds of the formula Ia.25 in which R⁸ is trifluoromethoxymethyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2749

Compounds of the formula Ia.25 in which R⁸ is methylthiomethyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2750

Compounds of the formula Ia.25 in which R⁸ is ethylthiomethyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2751

Compounds of the formula Ia.25 in which R⁸ is trifluoromethylthiomethyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2752

Compounds of the formula Ia.25 in which R⁸ is methylsulfinylmethyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2753

Compounds of the formula Ia.25 in which R⁸ is ethylsulfinylmethyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2754

Compounds of the formula Ia.25 in which R⁸ istrifluoromethylsulfinylmethyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2755

Compounds of the formula Ia.25 in which R⁸ is methylsulfonylmethyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2756

Compounds of the formula Ia.25 in which R⁸ is ethylsulfonylmethyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2757

Compounds of the formula Ia.25 in which R⁸ istrifluoromethylsulfonylmethyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2758

Compounds of the formula Ia.25 in which R⁸ is —CH(CH₃)—SO₂—CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2759

Compounds of the formula Ia.25 in which R⁸ is —C(CH₃)₂—SO₂—CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2760

Compounds of the formula Ia.25 in which R⁸ is —CH₂—N(CH₃)₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2761

Compounds of the formula Ia.25 in which R⁸ is —CH₂—CH₂—N(CH₃)₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2762

Compounds of the formula Ia.25 in which R⁸ is —N(H)CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2763

Compounds of the formula Ia.25 in which R⁸ is —N(H)CH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2764

Compounds of the formula Ia.25 in which R⁸ is —N(H)CH₂CHF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2765

Compounds of the formula Ia.25 in which R⁸ is —N(H)CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2766

Compounds of the formula Ia.25 in which R⁸ is —N(H)CH₂CH═CH₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2767

Compounds of the formula Ia.25 in which R⁸ is —N(H)CH₂C≡CH, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2768

Compounds of the formula Ia.25 in which R⁸ is —N(H)CH₂CN, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2769

Compounds of the formula Ia.25 in which R⁸ is —N(H)-cyclopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2770

Compounds of the formula Ia.25 in which R⁸ is—N(H)-(1-cyanocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2771

Compounds of the formula Ia.25 in which R⁸ is NH₂, and the combinationof R^(2a), R^(2b), R^(2b) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 2772

Compounds of the formula Ia.25 in which R⁸ is —N(H)—CH₂-cyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2773

Compounds of the formula Ia.25 in which R⁸ is—N(H)—CH₂-(1-cyanocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2774

Compounds of the formula Ia.25 in which R⁸ is —C(O)—N(H)CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2775

Compounds of the formula Ia.25 in which R⁸ is —C(O)—N(H)CH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2776

Compounds of the formula Ia.25 in which R⁸ is —C(O)—N(H)CH₂CHF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2777

Compounds of the formula Ia.25 in which R⁸ is —C(O)—N(H)CH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2778

Compounds of the formula Ia.25 in which R⁸ is —C(O)—N(H)CH₂CH═CH₂, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2779

Compounds of the formula Ia.25 in which R⁸ is —C(O)—N(H)CH₂C≡CH, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2780

Compounds of the formula Ia.25 in which R⁸ is —C(O)—N(H)CH₂CN, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2781

Compounds of the formula Ia.25 in which R⁸ is —C(O)—N(H)-cyclopropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2782

Compounds of the formula Ia.25 in which R⁸ is—C(O)—N(H)-(1-cyanocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2783

Compounds of the formula Ia.25 in which R⁸ is—C(O)—N(H)—CH₂-cyclopropyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2784

Compounds of the formula Ia.25 in which R⁸ is—C(O)—N(H)—CH₂-(1-cyanocyclopropyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 2785

Compounds of the formula Ia.25 in which R⁸ is —CH₂—C(O)—N(H)CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2786

Compounds of the formula Ia.25 in which R⁸ is —CH₂—C(O)—N(H)CH₂CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2787

Compounds of the formula Ia.25 in which R⁸ is —CH₂—C(O)—N(H)CH₂CHF₂, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2788

Compounds of the formula Ia.25 in which R⁸ is —CH₂—C(O)—N(H)CH₂CF₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2789

Compounds of the formula Ia.25 in which R⁸ is —CH₂—C(O)—N(H)CH₂CH═CH₂,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2790

Compounds of the formula Ia.25 in which R⁸ is —CH₂—C(O)—N(H)CH₂C≡CH, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2791

Compounds of the formula Ia.25 in which R⁸ is —CH₂—C(O)—N(H)CH₂CN, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2792

Compounds of the formula Ia.25 in which R⁸ is—CH₂—C(O)—N(H)-cyclopropyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2793

Compounds of the formula Ia.25 in which R⁸ is—CH₂—C(O)—N(H)-(1-cyanocyclopropyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 2794

Compounds of the formula Ia.25 in which R⁸ is—CH₂—C(O)—N(H)—CH₂-cyclopropyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2795

Compounds of the formula Ia.25 in which R⁸ is—CH₂—C(O)—N(H)—CH₂-(1-cyanocyclopropyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 2796

Compounds of the formula Ia.25 in which R⁸ is —NH—C(O)—N(H)CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2797

Compounds of the formula Ia.25 in which R⁸ is —NH—C(O)—N(H)CH₂CH₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2798

Compounds of the formula Ia.25 in which R⁸ is —NH—C(O)—N(H)CH₂CHF₂, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2799

Compounds of the formula Ia.25 in which R⁸ is —NH—C(O)—N(H)CH₂CF₃, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2800

Compounds of the formula Ia.25 in which R⁸ is —NH—C(O)—N(H)CH₂CH═CH₂,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2801

Compounds of the formula Ia.25 in which R⁸ is —NH—C(O)—N(H)CH₂C≡CH, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2802

Compounds of the formula Ia.25 in which R⁸ is —NH—C(O)—N(H)CH₂CN, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2803

Compounds of the formula Ia.25 in which R⁸ is —NH—C(O)—N(H)-cyclopropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2804

Compounds of the formula Ia.25 in which R⁸ is—NH—C(O)—N(H)-(1-cyanocyclopropyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 2805

Compounds of the formula Ia.25 in which R⁸ is—NH—C(O)—N(H)—CH₂-cyclopropyl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2806

Compounds of the formula Ia.25 in which R⁸ is—NH—C(O)—N(H)—CH₂-(1-cyanocyclopropyl), and the combination of R^(2a),R^(2b), R^(2c) and R^(4b) for a compound corresponds in each case to onerow of Table A

Table 2807

Compounds of the formula Ia.25 in which R⁸ is —CH═N—OCH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2808

Compounds of the formula Ia.25 in which R⁸ is —CH═N—OCH₂CH₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2809

Compounds of the formula Ia.25 in which R⁸ is —CH═N—OCH₂CHF₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2810

Compounds of the formula Ia.25 in which R⁸ is —CH═N—OCH₂CF₃, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2811

Compounds of the formula Ia.25 in which R⁸ is —CH═N—OCH₂CH═CH₂, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2812

Compounds of the formula Ia.25 in which R⁸ is —CH═N—OCH₂C≡CH, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2813

Compounds of the formula Ia.25 in which R⁸ is —CH═N—OCH₂CN, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2814

Compounds of the formula Ia.25 in which R⁸ is —CH═N—O-cyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2815

Compounds of the formula Ia.25 in which R⁸ is—CH═N—O-(1-cyanocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 2816

Compounds of the formula Ia.25 in which R⁸ is —CH═N—O—CH₂-cyclopropyl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 2817

Compounds of the formula Ia.25 in which R⁸ is—CH═N—O—CH₂-(1-cyanocyclopropyl), and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Tables 2818 to 2956

Compounds of the formula Ia.26 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 2957 to 3095

Compounds of the formula Ia.27 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 3096 to 3234

Compounds of the formula Ia.28 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 3235 to 3373

Compounds of the formula Ia.29 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 3374 to 3512

Compounds of the formula Ia.30 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 3513 to 3651

Compounds of the formula Ia.31 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 3652 to 3790

Compounds of the formula Ia.32 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 3791 to 3929

Compounds of the formula Ia.33 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 3930 to 4068

Compounds of the formula Ia.34 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 4069 to 4207

Compounds of the formula Ia.35 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Tables 4208 to 4346

Compounds of the formula Ia.36 in which R⁸ is as defined in tables 2679to 2817, and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for acompound corresponds in each case to one row of Table A

Table 4347

Compounds of the formula Ia.37 in which A⁴ is 1H-pyrrol-1-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4348

Compounds of the formula Ia.37 in which A⁴ is 1H-3-chloro-pyrrol-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4349

Compounds of the formula Ia.37 in which A⁴ is 1H-3-cyano-pyrrol-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4350

Compounds of the formula Ia.37 in which A⁴ is 1H-pyrazol-1-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4351

Compounds of the formula Ia.37 in which A⁴ is 1H-4-cloro-pyrazol-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4352

Compounds of the formula Ia.37 in which A⁴ is 1H-4-cyano-pyrazol-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4353

Compounds of the formula Ia.37 in which A⁴ is 1H-imidazol-1-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4354

Compounds of the formula Ia.37 in which A⁴ is 1H-4-chloro-imidazol-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4355

Compounds of the formula Ia.37 in which A⁴ is 1H-4-cyano-imidazol-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4356

Compounds of the formula Ia.37 in which A⁴ is 1H-[1,2,4]-triazol-1-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4357

Compounds of the formula Ia.37 in which A⁴ is1H-[1,2,4]-3-chloro-triazol-1-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 4358

Compounds of the formula Ia.37 in which A⁴ is1H-[1,2,4]-3-cyano-triazol-1-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 4359

Compounds of the formula Ia.37 in which A⁴ is 1H-1-methyl-pyrrol-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4360

Compounds of the formula Ia.37 in which A⁴ is 1H-1-methyl-pyrrol-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4361

Compounds of the formula Ia.37 in which A⁴ is 1H-1-methyl-pyrazol-4-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4362

Compounds of the formula Ia.37 in which A⁴ is 1H-1-methyl-pyrazol-5-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4363

Compounds of the formula Ia.37 in which A⁴ is1H-1,3-dimethyl-pyrazol-5-yl, and the combination of R^(2a), R^(2b),R^(2c) and R^(4b) for a compound corresponds in each case to one row ofTable A

Table 4364

Compounds of the formula Ia.37 in which A⁴ is1H-1-methyl-3-trifluoromethyl-pyrazol-5-yl, and the combination ofR^(2a), R^(2b), R^(2c) and R^(4b) for a compound corresponds in eachcase to one row of Table A

Table 4365

Compounds of the formula Ia.37 in which A⁴ is 1H-1-[1,2,3]-triazol-5-yl,and the combination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4366

Compounds of the formula Ia.37 in which A⁴ is pyridin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4367

Compounds of the formula Ia.37 in which A⁴ is pyridin-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4368

Compounds of the formula Ia.37 in which A⁴ is pyridin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4369

Compounds of the formula Ia.37 in which A⁴ is pyrimidin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4370

Compounds of the formula Ia.37 in which A⁴ is pyrimidin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4371

Compounds of the formula Ia.37 in which A⁴ is pyrimidin-5-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

Table 4372

Compounds of the formula Ia.37 in which A⁴ is pyrazin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R^(4b) for a compoundcorresponds in each case to one row of Table A

TABLE A No. R^(2a) R^(2b) R^(2c) R^(4b) A-1 F H F H A-2 F F F H A-3 F ClF H A-4 F Br F H A-5 F H Cl H A-6 F H Br H A-7 Cl H Cl H A-8 Cl Cl Cl HA-9 Cl F Cl H A-10 Cl Br Cl H A-11 Cl H Br H A-12 Br H Br H A-13 Br F BrH A-14 Br Cl Br H A-15 CF₃ H F H A-16 CF₃ H Cl H A-17 CF₃ H Br H A-18CF₃ H CF₃ H A-19 CF₃ F F H A-20 CF₃ Cl Cl H A-21 CF₃ Br Br H A-22 SF₅ HF H A-23 SF₅ H Cl H A-24 SF₅ H Br H A-25 SF₅ H CF₃ H A-26 SF₅ H H H A-27CF₃ H H H A-28 Br H H H A-29 Cl H H H A-30 F H H H A-31 F H F CH₃ A-32 FF F CH₃ A-33 F Cl F CH₃ A-34 F Br F CH₃ A-35 F H Cl CH₃ A-36 F H Br CH₃A-37 Cl H Cl CH₃ A-38 Cl Cl Cl CH₃ A-39 Cl F Cl CH₃ A-40 Cl Br Cl CH₃A-41 Cl H Br CH₃ A-42 Br H Br CH₃ A-43 Br F Br CH₃ A-44 Br Cl Br CH₃A-45 CF₃ H F CH₃ A-46 CF₃ H Cl CH₃ A-47 CF₃ H Br CH₃ A-48 CF₃ H CF₃ CH₃A-49 CF₃ F F CH₃ A-50 CF₃ Cl Cl CH₃ A-51 CF₃ Br Br CH₃ A-52 SF₅ H F CH₃A-53 SF₅ H Cl CH₃ A-54 SF₅ H Br CH₃ A-55 SF₅ H CF₃ CH₃ A-56 SF₅ H H CH₃A-57 CF₃ H H CH₃ A-58 Br H H CH₃ A-59 Cl H H CH₃ A-60 F H H CH₃ A-61 F HF CH₂CH₃ A-62 F F F CH₂CH₃ A-63 F Cl F CH₂CH₃ A-64 F Br F CH₂CH₃ A-65 FH Cl CH₂CH₃ A-66 F H Br CH₂CH₃ A-67 Cl H Cl CH₂CH₃ A-68 Cl Cl Cl CH₂CH₃A-69 Cl F Cl CH₂CH₃ A-70 Cl Br Cl CH₂CH₃ A-71 Cl H Br CH₂CH₃ A-72 Br HBr CH₂CH₃ A-73 Br F Br CH₂CH₃ A-74 Br Cl Br CH₂CH₃ A-75 CF₃ H F CH₂CH₃A-76 CF₃ H Cl CH₂CH₃ A-77 CF₃ H Br CH₂CH₃ A-78 CF₃ H CF₃ CH₂CH₃ A-79 CF₃F F CH₂CH₃ A-80 CF₃ Cl Cl CH₂CH₃ A-81 CF₃ Br Br CH₂CH₃ A-82 SF₅ H FCH₂CH₃ A-83 SF₅ H Cl CH₂CH₃ A-84 SF₅ H Br CH₂CH₃ A-85 SF₅ H CF₃ CH₂CH₃A-86 SF₅ H H CH₂CH₃ A-87 CF₃ H H CH₂CH₃ A-88 Br H H CH₂CH₃ A-89 Cl H HCH₂CH₃ A-90 F H H CH₂CH₃ A-91 F H F CH(CH₃)₂ A-92 F F F CH(CH₃)₂ A-93 FCl F CH(CH₃)₂ A-94 F Br F CH(CH₃)₂ A-95 F H Cl CH(CH₃)₂ A-96 F H BrCH(CH₃)₂ A-97 Cl H Cl CH(CH₃)₂ A-98 Cl Cl Cl CH(CH₃)₂ A-99 Cl F ClCH(CH₃)₂ A-100 Cl Br Cl CH(CH₃)₂ A-101 Cl H Br CH(CH₃)₂ A-102 Br H BrCH(CH₃)₂ A-103 Br F Br CH(CH₃)₂ A-104 Br Cl Br CH(CH₃)₂ A-105 CF₃ H FCH(CH₃)₂ A-106 CF₃ H Cl CH(CH₃)₂ A-107 CF₃ H Br CH(CH₃)₂ A-108 CF₃ H CF₃CH(CH₃)₂ A-109 CF₃ F F CH(CH₃)₂ A-110 CF₃ Cl Cl CH(CH₃)₂ A-111 CF₃ Br BrCH(CH₃)₂ A-112 SF₅ H F CH(CH₃)₂ A-113 SF₅ H Cl CH(CH₃)₂ A-114 SF₅ H BrCH(CH₃)₂ A-115 SF₅ H CF₃ CH(CH₃)₂ A-116 SF₅ H H CH(CH₃)₂ A-117 CF₃ H HCH(CH₃)₂ A-118 Br H H CH(CH₃)₂ A-119 Cl H H CH(CH₃)₂ A-120 F H HCH(CH₃)₂ A-121 F H F CHF₂ A-122 F F F CHF₂ A-123 F Cl F CHF₂ A-124 F BrF CHF₂ A-125 F H Cl CHF₂ A-126 F H Br CHF₂ A-127 Cl H Cl CHF₂ A-128 ClCl Cl CHF₂ A-129 Cl F Cl CHF₂ A-130 Cl Br Cl CHF₂ A-131 Cl H Br CHF₂A-132 Br H Br CHF₂ A-133 Br F Br CHF₂ A-134 Br Cl Br CHF₂ A-135 CF₃ H FCHF₂ A-136 CF₃ H Cl CHF₂ A-137 CF₃ H Br CHF₂ A-138 CF₃ H CF₃ CHF₂ A-139CF₃ F F CHF₂ A-140 CF₃ Cl Cl CHF₂ A-141 CF₃ Br Br CHF₂ A-142 SF₅ H FCHF₂ A-143 SF₅ H Cl CHF₂ A-144 SF₅ H Br CHF₂ A-145 SF₅ H CF₃ CHF₂ A-146SF₅ H H CHF₂ A-147 CF₃ H H CHF₂ A-148 Br H H CHF₂ A-149 Cl H H CHF₂A-150 F H H CHF₂ A-151 F H F CF₃ A-152 F F F CF₃ A-153 F Cl F CF₃ A-154F Br F CF₃ A-155 F H Cl CF₃ A-156 F H Br CF₃ A-157 Cl H Cl CF₃ A-158 ClCl Cl CF₃ A-159 Cl F Cl CF₃ A-160 Cl Br Cl CF₃ A-161 Cl H Br CF₃ A-162Br H Br CF₃ A-163 Br F Br CF₃ A-164 Br Cl Br CF₃ A-165 CF₃ H F CF₃ A-166CF₃ H Cl CF₃ A-167 CF₃ H Br CF₃ A-168 CF₃ H CF₃ CF₃ A-169 CF₃ F F CF₃A-170 CF₃ Cl Cl CF₃ A-171 CF₃ Br Br CF₃ A-172 SF₅ H F CF₃ A-173 SF₅ H ClCF₃ A-174 SF₅ H Br CF₃ A-175 SF₅ H CF₃ CF₃ A-176 SF₅ H H CF₃ A-177 CF₃ HH CF₃ A-178 Br H H CF₃ A-179 Cl H H CF₃ A-180 F H H CF₃ A-181 F H FCH₂—CH═CH₂ A-182 F F F CH₂—CH═CH₂ A-183 F Cl F CH₂—CH═CH₂ A-184 F Br FCH₂—CH═CH₂ A-185 F H Cl CH₂—CH═CH₂ A-186 F H Br CH₂—CH═CH₂ A-187 Cl H ClCH₂—CH═CH₂ A-188 Cl Cl Cl CH₂—CH═CH₂ A-189 Cl F Cl CH₂—CH═CH₂ A-190 ClBr Cl CH₂—CH═CH₂ A-191 Cl H Br CH₂—CH═CH₂ A-192 Br H Br CH₂—CH═CH₂ A-193Br F Br CH₂—CH═CH₂ A-194 Br Cl Br CH₂—CH═CH₂ A-195 CF₃ H F CH₂—CH═CH₂A-196 CF₃ H Cl CH₂—CH═CH₂ A-197 CF₃ H Br CH₂—CH═CH₂ A-198 CF₃ H CF₃CH₂—CH═CH₂ A-199 CF₃ F F CH₂—CH═CH₂ A-200 CF₃ Cl Cl CH₂—CH═CH₂ A-201 CF₃Br Br CH₂—CH═CH₂ A-202 SF₅ H F CH₂—CH═CH₂ A-203 SF₅ H Cl CH₂—CH═CH₂A-204 SF₅ H Br CH₂—CH═CH₂ A-205 SF₅ H CF₃ CH₂—CH═CH₂ A-206 SF₅ H HCH₂—CH═CH₂ A-207 CF₃ H H CH₂—CH═CH₂ A-208 Br H H CH₂—CH═CH₂ A-209 Cl H HCH₂—CH═CH₂ A-210 F H H CH₂—CH═CH₂ A-211 F H F CH═CH₂ A-212 F F F CH═CH₂A-213 F Cl F CH═CH₂ A-214 F Br F CH═CH₂ A-215 F H Cl CH═CH₂ A-216 F H BrCH═CH₂ A-217 Cl H Cl CH═CH₂ A-218 Cl Cl Cl CH═CH₂ A-219 Cl F Cl CH═CH₂A-220 Cl Br Cl CH═CH₂ A-221 Cl H Br CH═CH₂ A-222 Br H Br CH═CH₂ A-223 BrF Br CH═CH₂ A-224 Br Cl Br CH═CH₂ A-225 CF₃ H F CH═CH₂ A-226 CF₃ H ClCH═CH₂ A-227 CF₃ H Br CH═CH₂ A-228 CF₃ H CF₃ CH═CH₂ A-229 CF₃ F F CH═CH₂A-230 CF₃ Cl Cl CH═CH₂ A-231 CF₃ Br Br CH═CH₂ A-232 SF₅ H F CH═CH₂ A-233SF₅ H Cl CH═CH₂ A-234 SF₅ H Br CH═CH₂ A-235 SF₅ H CF₃ CH═CH₂ A-236 SF₅ HH CH═CH₂ A-237 CF₃ H H CH═CH₂ A-238 Br H H CH═CH₂ A-239 Cl H H CH═CH₂A-240 F H H CH═CH₂ A-241 F H F C≡CH A-242 F F F C≡CH A-243 F Cl F C≡CHA-244 F Br F C≡CH A-245 F H Cl C≡CH A-246 F H Br C≡CH A-247 Cl H Cl C≡CHA-248 Cl Cl Cl C≡CH A-249 Cl F Cl C≡CH A-250 Cl Br Cl C≡CH A-251 Cl H BrC≡CH A-252 Br H Br C≡CH A-253 Br F Br C≡CH A-254 Br Cl Br C≡CH A-255 CF₃H F C≡CH A-256 CF₃ H Cl C≡CH A-257 CF₃ H Br C≡CH A-258 CF₃ H CF₃ C≡CHA-259 CF₃ F F C≡CH A-260 CF₃ Cl Cl C≡CH A-261 CF₃ Br Br C≡CH A-262 SF₅ HF C≡CH A-263 SF₅ H Cl C≡CH A-264 SF₅ H Br C≡CH A-265 SF₅ H CF₃ C≡CHA-266 SF₅ H H C≡CH A-267 CF₃ H H C≡CH A-268 Br H H C≡CH A-269 Cl H HC≡CH A-270 F H H C≡CH A-271 F H F ^(c)C₃H₅* A-272 F F F ^(c)C₃H₅* A-273F Cl F ^(c)C₃H₅* A-274 F Br F ^(c)C₃H₅* A-275 F H Cl ^(c)C₃H₅* A-276 F HBr ^(c)C₃H₅* A-277 Cl H Cl ^(c)C₃H₅* A-278 Cl Cl Cl ^(c)C₃H₅* A-279 Cl FCl ^(c)C₃H₅* A-280 Cl Br Cl ^(c)C₃H₅* A-281 Cl H Br ^(c)C₃H₅* A-282 Br HBr ^(c)C₃H₅* A-283 Br F Br ^(c)C₃H₅* A-284 Br Cl Br ^(c)C₃H₅* A-285 CF₃H F ^(c)C₃H₅* A-286 CF₃ H Cl ^(c)C₃H₅* A-287 CF₃ H Br ^(c)C₃H₅* A-288CF₃ H CF₃ ^(c)C₃H₅* A-289 CF₃ F F ^(c)C₃H₅* A-290 CF₃ Cl Cl ^(c)C₃H₅*A-291 CF₃ Br Br ^(c)C₃H₅* A-292 SF₅ H F ^(c)C₃H₅* A-293 SF₅ H Cl^(c)C₃H₅* A-294 SF₅ H Br ^(c)C₃H₅* A-295 SF₅ H CF₃ ^(c)C₃H₅* A-296 SF₅ HH ^(c)C₃H₅* A-297 CF₃ H H ^(c)C₃H₅* A-298 Br H H ^(c)C₃H₅* A-299 Cl H H^(c)C₃H₅* A-300 F H H ^(c)C₃H₅* A-301 F H F F A-302 F F F F A-303 F Cl FF A-304 F Br F F A-305 F H Cl F A-306 F H Br F A-307 Cl H Cl F A-308 ClCl Cl F A-309 Cl F Cl F A-310 Cl Br Cl F A-311 Cl H Br F A-312 Br H Br FA-313 Br F Br F A-314 Br Cl Br F A-315 CF₃ H F F A-316 CF₃ H Cl F A-317CF₃ H Br F A-318 CF₃ H CF₃ F A-319 CF₃ F F F A-320 CF₃ Cl Cl F A-321 CF₃Br Br F A-322 SF₅ H F F A-323 SF₅ H Cl F A-324 SF₅ H Br F A-325 SF₅ HCF₃ F A-326 SF₅ H H F A-327 CF₃ H H F A-328 Br H H F A-329 Cl H H FA-330 F H H F A-331 F H F Cl A-332 F F F Cl A-333 F Cl F Cl A-334 F Br FCl A-335 F H Cl Cl A-336 F H Br Cl A-337 Cl H Cl Cl A-338 Cl Cl Cl ClA-339 Cl F Cl Cl A-340 Cl Br Cl Cl A-341 Cl H Br Cl A-342 Br H Br ClA-343 Br F Br Cl A-344 Br Cl Br Cl A-345 CF₃ H F Cl A-346 CF₃ H Cl ClA-347 CF₃ H Br Cl A-348 CF₃ H CF₃ Cl A-349 CF₃ F F Cl A-350 CF₃ Cl Cl ClA-351 CF₃ Br Br Cl A-352 SF₅ H F Cl A-353 SF₅ H Cl Cl A-354 SF₅ H Br ClA-355 SF₅ H CF₃ Cl A-356 SF₅ H H Cl A-357 CF₃ H H Cl A-358 Br H H ClA-359 Cl H H Cl A-360 F H H Cl A-361 F H F Br A-362 F F F Br A-363 F ClF Br A-364 F Br F Br A-365 F H Cl Br A-366 F H Br Br A-367 Cl H Cl BrA-368 Cl Cl Cl Br A-369 Cl F Cl Br A-370 Cl Br Cl Br A-371 Cl H Br BrA-372 Br H Br Br A-373 Br F Br Br A-374 Br Cl Br Br A-375 CF₃ H F BrA-376 CF₃ H Cl Br A-377 CF₃ H Br Br A-378 CF₃ H CF₃ Br A-379 CF₃ F F BrA-380 CF₃ Cl Cl Br A-381 CF₃ Br Br Br A-382 SF₅ H F Br A-383 SF₅ H Cl BrA-384 SF₅ H Br Br A-385 SF₅ H CF₃ Br A-386 SF₅ H H Br A-387 CF₃ H H BrA-388 Br H H Br A-389 Cl H H Br A-390 F H H Br A-391 F H F CN A-392 F FF CN A-393 F Cl F CN A-394 F Br F CN A-395 F H Cl CN A-396 F H Br CNA-397 Cl H Cl CN A-398 Cl Cl Cl CN A-399 Cl F Cl CN A-400 Cl Br Cl CNA-401 Cl H Br CN A-402 Br H Br CN A-403 Br F Br CN A-404 Br Cl Br CNA-405 CF₃ H F CN A-406 CF₃ H Cl CN A-407 CF₃ H Br CN A-408 CF₃ H CF₃ CNA-409 CF₃ F F CN A-410 CF₃ Cl Cl CN A-411 CF₃ Br Br CN A-412 SF₅ H F CNA-413 SF₅ H Cl CN A-414 SF₅ H Br CN A-415 SF₅ H CF₃ CN A-416 SF₅ H H CNA-417 CF₃ H H CN A-418 Br H H CN A-419 Cl H H CN A-420 F H H CN A-421 FH F OCH₃ A-422 F F F OCH₃ A-423 F Cl F OCH₃ A-424 F Br F OCH₃ A-425 F HCl OCH₃ A-426 F H Br OCH₃ A-427 Cl H Cl OCH₃ A-428 Cl Cl Cl OCH₃ A-429Cl F Cl OCH₃ A-430 Cl Br Cl OCH₃ A-431 Cl H Br OCH₃ A-432 Br H Br OCH₃A-433 Br F Br OCH₃ A-434 Br Cl Br OCH₃ A-435 CF₃ H F OCH₃ A-436 CF₃ H ClOCH₃ A-437 CF₃ H Br OCH₃ A-438 CF₃ H CF₃ OCH₃ A-439 CF₃ F F OCH₃ A-440CF₃ Cl Cl OCH₃ A-441 CF₃ Br Br OCH₃ A-442 SF₅ H F OCH₃ A-443 SF₅ H ClOCH₃ A-444 SF₅ H Br OCH₃ A-445 SF₅ H CF₃ OCH₃ A-446 SF₅ H H OCH₃ A-447CF₃ H H OCH₃ A-448 Br H H OCH₃ A-449 Cl H H OCH₃ A-450 F H H OCH₃ A-451F H F OCH₂CH₃ A-452 F F F OCH₂CH₃ A-453 F Cl F OCH₂CH₃ A-454 F Br FOCH₂CH₃ A-455 F H Cl OCH₂CH₃ A-456 F H Br OCH₂CH₃ A-457 Cl H Cl OCH₂CH₃A-458 Cl Cl Cl OCH₂CH₃ A-459 Cl F Cl OCH₂CH₃ A-460 Cl Br Cl OCH₂CH₃A-461 Cl H Br OCH₂CH₃ A-462 Br H Br OCH₂CH₃ A-463 Br F Br OCH₂CH₃ A-464Br Cl Br OCH₂CH₃ A-465 CF₃ H F OCH₂CH₃ A-466 CF₃ H Cl OCH₂CH₃ A-467 CF₃H Br OCH₂CH₃ A-468 CF₃ H CF₃ OCH₂CH₃ A-469 CF₃ F F OCH₂CH₃ A-470 CF₃ ClCl OCH₂CH₃ A-471 CF₃ Br Br OCH₂CH₃ A-472 SF₅ H F OCH₂CH₃ A-473 SF₅ H ClOCH₂CH₃ A-474 SF₅ H Br OCH₂CH₃ A-475 SF₅ H CF₃ OCH₂CH₃ A-476 SF₅ H HOCH₂CH₃ A-477 CF₃ H H OCH₂CH₃ A-478 Br H H OCH₂CH₃ A-479 Cl H H OCH₂CH₃A-480 F H H OCH₂CH₃ A-481 F H F OCH(CH₃)₂ A-482 F F F OCH(CH₃)₂ A-483 FCl F OCH(CH₃)₂ A-484 F Br F OCH(CH₃)₂ A-485 F H Cl OCH(CH₃)₂ A-486 F HBr OCH(CH₃)₂ A-487 Cl H Cl OCH(CH₃)₂ A-488 Cl Cl Cl OCH(CH₃)₂ A-489 Cl FCl OCH(CH₃)₂ A-490 Cl Br Cl OCH(CH₃)₂ A-491 Cl H Br OCH(CH₃)₂ A-492 Br HBr OCH(CH₃)₂ A-493 Br F Br OCH(CH₃)₂ A-494 Br Cl Br OCH(CH₃)₂ A-495 CF₃H F OCH(CH₃)₂ A-496 CF₃ H Cl OCH(CH₃)₂ A-497 CF₃ H Br OCH(CH₃)₂ A-498CF₃ H CF₃ OCH(CH₃)₂ A-499 CF₃ F F OCH(CH₃)₂ A-500 CF₃ Cl Cl OCH(CH₃)₂A-501 CF₃ Br Br OCH(CH₃)₂ A-502 SF₅ H F OCH(CH₃)₂ A-503 SF₅ H ClOCH(CH₃)₂ A-504 SF₅ H Br OCH(CH₃)₂ A-505 SF₅ H CF₃ OCH(CH₃)₂ A-506 SF₅ HH OCH(CH₃)₂ A-507 CF₃ H H OCH(CH₃)₂ A-508 Br H H OCH(CH₃)₂ A-509 Cl H HOCH(CH₃)₂ A-510 F H H OCH(CH₃)₂ A-511 F H F OCH₂CH═CH₂ A-512 F F FOCH₂CH═CH₂ A-513 F Cl F OCH₂CH═CH₂ A-514 F Br F OCH₂CH═CH₂ A-515 F H ClOCH₂CH═CH₂ A-516 F H Br OCH₂CH═CH₂ A-517 Cl H Cl OCH₂CH═CH₂ A-518 Cl ClCl OCH₂CH═CH₂ A-519 Cl F Cl OCH₂CH═CH₂ A-520 Cl Br Cl OCH₂CH═CH₂ A-521Cl H Br OCH₂CH═CH₂ A-522 Br H Br OCH₂CH═CH₂ A-523 Br F Br OCH₂CH═CH₂A-524 Br Cl Br OCH₂CH═CH₂ A-525 CF₃ H F OCH₂CH═CH₂ A-526 CF₃ H ClOCH₂CH═CH₂ A-527 CF₃ H Br OCH₂CH═CH₂ A-528 CF₃ H CF₃ OCH₂CH═CH₂ A-529CF₃ F F OCH₂CH═CH₂ A-530 CF₃ Cl Cl OCH₂CH═CH₂ A-531 CF₃ Br Br OCH₂CH═CH₂A-532 SF₅ H F OCH₂CH═CH₂ A-533 SF₅ H Cl OCH₂CH═CH₂ A-534 SF₅ H BrOCH₂CH═CH₂ A-535 SF₅ H CF₃ OCH₂CH═CH₂ A-536 SF₅ H H OCH₂CH═CH₂ A-537 CF₃H H OCH₂CH═CH₂ A-538 Br H H OCH₂CH═CH₂ A-539 Cl H H OCH₂CH═CH₂ A-540 F HH OCH₂CH═CH₂ A-541 F H F O—^(c)C₃H₅* A-542 F F F O—^(c)C₃H₅* A-543 F ClF O—^(c)C₃H₅* A-544 F Br F O—^(c)C₃H₅* A-545 F H Cl O—^(c)C₃H₅* A-546 FH Br O—^(c)C₃H₅* A-547 Cl H Cl O—^(c)C₃H₅* A-548 Cl Cl Cl O—^(c)C₃H₅*A-549 Cl F Cl O—^(c)C₃H₅* A-550 Cl Br Cl O—^(c)C₃H₅* A-551 Cl H BrO—^(c)C₃H₅* A-552 Br H Br O—^(c)C₃H₅* A-553 Br F Br O—^(c)C₃H₅* A-554 BrCl Br O—^(c)C₃H₅* A-555 CF₃ H F O—^(c)C₃H₅* A-556 CF₃ H Cl O—^(c)C₃H₅*A-557 CF₃ H Br O—^(c)C₃H₅* A-558 CF₃ H CF₃ O—^(c)C₃H₅* A-559 CF₃ F FO—^(c)C₃H₅* A-560 CF₃ Cl Cl O—^(c)C₃H₅* A-561 CF₃ Br Br O—^(c)C₃H₅*A-562 SF₅ H F O—^(c)C₃H₅* A-563 SF₅ H Cl O—^(c)C₃H₅* A-564 SF₅ H BrO—^(c)C₃H₅* A-565 SF₅ H CF₃ O—^(c)C₃H₅* A-566 SF₅ H H O—^(c)C₃H₅* A-567CF₃ H H O—^(c)C₃H₅* A-568 Br H H O—^(c)C₃H₅* A-569 Cl H H O—^(c)C₃H₅*A-570 F H H O—^(c)C₃H₅* A-571 F H F OCHF₂ A-572 F F F OCHF₂ A-573 F Cl FOCHF₂ A-574 F Br F OCHF₂ A-575 F H Cl OCHF₂ A-576 F H Br OCHF₂ A-577 ClH Cl OCHF₂ A-578 Cl Cl Cl OCHF₂ A-579 Cl F Cl OCHF₂ A-580 Cl Br Cl OCHF₂A-581 Cl H Br OCHF₂ A-582 Br H Br OCHF₂ A-583 Br F Br OCHF₂ A-584 Br ClBr OCHF₂ A-585 CF₃ H F OCHF₂ A-586 CF₃ H Cl OCHF₂ A-587 CF₃ H Br OCHF₂A-588 CF₃ H CF₃ OCHF₂ A-589 CF₃ F F OCHF₂ A-590 CF₃ Cl Cl OCHF₂ A-591CF₃ Br Br OCHF₂ A-592 SF₅ H F OCHF₂ A-593 SF₅ H Cl OCHF₂ A-594 SF₅ H BrOCHF₂ A-595 SF₅ H CF₃ OCHF₂ A-596 SF₅ H H OCHF₂ A-597 CF₃ H H OCHF₂A-598 Br H H OCHF₂ A-599 Cl H H OCHF₂ A-600 F H H OCHF₂ A-601 F H F OCF₃A-602 F F F OCF₃ A-603 F Cl F OCF₃ A-604 F Br F OCF₃ A-605 F H Cl OCF₃A-606 F H Br OCF₃ A-607 Cl H Cl OCF₃ A-608 Cl Cl Cl OCF₃ A-609 Cl F ClOCF₃ A-610 Cl Br Cl OCF₃ A-611 Cl H Br OCF₃ A-612 Br H Br OCF₃ A-613 BrF Br OCF₃ A-614 Br Cl Br OCF₃ A-615 CF₃ H F OCF₃ A-616 CF₃ H Cl OCF₃A-617 CF₃ H Br OCF₃ A-618 CF₃ H CF₃ OCF₃ A-619 CF₃ F F OCF₃ A-620 CF₃ ClCl OCF₃ A-621 CF₃ Br Br OCF₃ A-622 SF₅ H F OCF₃ A-623 SF₅ H Cl OCF₃A-624 SF₅ H Br OCF₃ A-625 SF₅ H CF₃ OCF₃ A-626 SF₅ H H OCF₃ A-627 CF₃ HH OCF₃ A-628 Br H H OCF₃ A-629 Cl H H OCF₃ A-630 F H H OCF₃ A-631 F H FOCH₂CF₃ A-632 F F F OCH₂CF₃ A-633 F Cl F OCH₂CF₃ A-634 F Br F OCH₂CF₃A-635 F H Cl OCH₂CF₃ A-636 F H Br OCH₂CF₃ A-637 Cl H Cl OCH₂CF₃ A-638 ClCl Cl OCH₂CF₃ A-639 Cl F Cl OCH₂CF₃ A-640 Cl Br Cl OCH₂CF₃ A-641 Cl H BrOCH₂CF₃ A-642 Br H Br OCH₂CF₃ A-643 Br F Br OCH₂CF₃ A-644 Br Cl BrOCH₂CF₃ A-645 CF₃ H F OCH₂CF₃ A-646 CF₃ H Cl OCH₂CF₃ A-647 CF₃ H BrOCH₂CF₃ A-648 CF₃ H CF₃ OCH₂CF₃ A-649 CF₃ F F OCH₂CF₃ A-650 CF₃ Cl ClOCH₂CF₃ A-651 CF₃ Br Br OCH₂CF₃ A-652 SF₅ H F OCH₂CF₃ A-653 SF₅ H ClOCH₂CF₃ A-654 SF₅ H Br OCH₂CF₃ A-655 SF₅ H CF₃ OCH₂CF₃ A-656 SF₅ H HOCH₂CF₃ A-657 CF₃ H H OCH₂CF₃ A-658 Br H H OCH₂CF₃ A-659 Cl H H OCH₂CF₃A-660 F H H OCH₂CF₃ A-661 F H F SCH₃ A-662 F F F SCH₃ A-663 F Cl F SCH₃A-664 F Br F SCH₃ A-665 F H Cl SCH₃ A-666 F H Br SCH₃ A-667 Cl H Cl SCH₃A-668 Cl Cl Cl SCH₃ A-669 Cl F Cl SCH₃ A-670 Cl Br Cl SCH₃ A-671 Cl H BrSCH₃ A-672 Br H Br SCH₃ A-673 Br F Br SCH₃ A-674 Br Cl Br SCH₃ A-675 CF₃H F SCH₃ A-676 CF₃ H Cl SCH₃ A-677 CF₃ H Br SCH₃ A-678 CF₃ H CF₃ SCH₃A-679 CF₃ F F SCH₃ A-680 CF₃ Cl Cl SCH₃ A-681 CF₃ Br Br SCH₃ A-682 SF₅ HF SCH₃ A-683 SF₅ H Cl SCH₃ A-684 SF₅ H Br SCH₃ A-685 SF₅ H CF₃ SCH₃A-686 SF₅ H H SCH₃ A-687 CF₃ H H SCH₃ A-688 Br H H SCH₃ A-689 Cl H HSCH₃ A-690 F H H SCH₃ A-691 F H F SCH₂CH₃ A-692 F F F SCH₂CH₃ A-693 F ClF SCH₂CH₃ A-694 F Br F SCH₂CH₃ A-695 F H Cl SCH₂CH₃ A-696 F H Br SCH₂CH₃A-697 Cl H Cl SCH₂CH₃ A-698 Cl Cl Cl SCH₂CH₃ A-699 Cl F Cl SCH₂CH₃ A-700Cl Br Cl SCH₂CH₃ A-701 Cl H Br SCH₂CH₃ A-702 Br H Br SCH₂CH₃ A-703 Br FBr SCH₂CH₃ A-704 Br Cl Br SCH₂CH₃ A-705 CF₃ H F SCH₂CH₃ A-706 CF₃ H ClSCH₂CH₃ A-707 CF₃ H Br SCH₂CH₃ A-708 CF₃ H CF₃ SCH₂CH₃ A-709 CF₃ F FSCH₂CH₃ A-710 CF₃ Cl Cl SCH₂CH₃ A-711 CF₃ Br Br SCH₂CH₃ A-712 SF₅ H FSCH₂CH₃ A-713 SF₅ H Cl SCH₂CH₃ A-714 SF₅ H Br SCH₂CH₃ A-715 SF₅ H CF₃SCH₂CH₃ A-716 SF₅ H H SCH₂CH₃ A-717 CF₃ H H SCH₂CH₃ A-718 Br H H SCH₂CH₃A-719 Cl H H SCH₂CH₃ A-720 F H H SCH₂CH₃ A-721 F H F SCH(CH₃)₂ A-722 F FF SCH(CH₃)₂ A-723 F Cl F SCH(CH₃)₂ A-724 F Br F SCH(CH₃)₂ A-725 F H ClSCH(CH₃)₂ A-726 F H Br SCH(CH₃)₂ A-727 Cl H Cl SCH(CH₃)₂ A-728 Cl Cl ClSCH(CH₃)₂ A-729 Cl F Cl SCH(CH₃)₂ A-730 Cl Br Cl SCH(CH₃)₂ A-731 Cl H BrSCH(CH₃)₂ A-732 Br H Br SCH(CH₃)₂ A-733 Br F Br SCH(CH₃)₂ A-734 Br Cl BrSCH(CH₃)₂ A-735 CF₃ H F SCH(CH₃)₂ A-736 CF₃ H Cl SCH(CH₃)₂ A-737 CF₃ HBr SCH(CH₃)₂ A-738 CF₃ H CF₃ SCH(CH₃)₂ A-739 CF₃ F F SCH(CH₃)₂ A-740 CF₃Cl Cl SCH(CH₃)₂ A-741 CF₃ Br Br SCH(CH₃)₂ A-742 SF₅ H F SCH(CH₃)₂ A-743SF₅ H Cl SCH(CH₃)₂ A-744 SF₅ H Br SCH(CH₃)₂ A-745 SF₅ H CF₃ SCH(CH₃)₂A-746 SF₅ H H SCH(CH₃)₂ A-747 CF₃ H H SCH(CH₃)₂ A-748 Br H H SCH(CH₃)₂A-749 Cl H H SCH(CH₃)₂ A-750 F H H SCH(CH₃)₂ A-751 F H F SCH₂CH═CH₂A-752 F F F SCH₂CH═CH₂ A-753 F Cl F SCH₂CH═CH₂ A-754 F Br F SCH₂CH═CH₂A-755 F H Cl SCH₂CH═CH₂ A-756 F H Br SCH₂CH═CH₂ A-757 Cl H Cl SCH₂CH═CH₂A-758 Cl Cl Cl SCH₂CH═CH₂ A-759 Cl F Cl SCH₂CH═CH₂ A-760 Cl Br ClSCH₂CH═CH₂ A-761 Cl H Br SCH₂CH═CH₂ A-762 Br H Br SCH₂CH═CH₂ A-763 Br FBr SCH₂CH═CH₂ A-764 Br Cl Br SCH₂CH═CH₂ A-765 CF₃ H F SCH₂CH═CH₂ A-766CF₃ H Cl SCH₂CH═CH₂ A-767 CF₃ H Br SCH₂CH═CH₂ A-768 CF₃ H CF₃ SCH₂CH═CH₂A-769 CF₃ F F SCH₂CH═CH₂ A-770 CF₃ Cl Cl SCH₂CH═CH₂ A-771 CF₃ Br BrSCH₂CH═CH₂ A-772 SF₅ H F SCH₂CH═CH₂ A-773 SF₅ H Cl SCH₂CH═CH₂ A-774 SF₅H Br SCH₂CH═CH₂ A-775 SF₅ H CF₃ SCH₂CH═CH₂ A-776 SF₅ H H SCH₂CH═CH₂A-777 CF₃ H H SCH₂CH═CH₂ A-778 Br H H SCH₂CH═CH₂ A-779 Cl H H SCH₂CH═CH₂A-780 F H H SCH₂CH═CH₂ A-781 F H F S—^(c)C₃H₅* A-782 F F F S—^(c)C₃H₅*A-783 F Cl F S—^(c)C₃H₅* A-784 F Br F S—^(c)C₃H₅* A-785 F H ClS—^(c)C₃H₅* A-786 F H Br S—^(c)C₃H₅* A-787 Cl H Cl S—^(c)C₃H₅* A-788 ClCl Cl S—^(c)C₃H₅* A-789 Cl F Cl S—^(c)C₃H₅* A-790 Cl Br Cl S—^(c)C₃H₅*A-791 Cl H Br S—^(c)C₃H₅* A-792 Br H Br S—^(c)C₃H₅* A-793 Br F BrS—^(c)C₃H₅* A-794 Br Cl Br S—^(c)C₃H₅* A-795 CF₃ H F S—^(c)C₃H₅* A-796CF₃ H Cl S—^(c)C₃H₅* A-797 CF₃ H Br S—^(c)C₃H₅* A-798 CF₃ H CF₃S—^(c)C₃H₅* A-799 CF₃ F F S—^(c)C₃H₅* A-800 CF₃ Cl Cl S—^(c)C₃H₅* A-801CF₃ Br Br S—^(c)C₃H₅* A-802 SF₅ H F S—^(c)C₃H₅* A-803 SF₅ H ClS—^(c)C₃H₅* A-804 SF₅ H Br S—^(c)C₃H₅* A-805 SF₅ H CF₃ S—^(c)C₃H₅* A-806SF₅ H H S—^(c)C₃H₅* A-807 CF₃ H H S—^(c)C₃H₅* A-808 Br H H S—^(c)C₃H₅*A-809 Cl H H S—^(c)C₃H₅* A-810 F H H S—^(c)C₃H₅* A-811 F H F SCF₃ A-812F F F SCF₃ A-813 F Cl F SCF₃ A-814 F Br F SCF₃ A-815 F H Cl SCF₃ A-816 FH Br SCF₃ A-817 Cl H Cl SCF₃ A-818 Cl Cl Cl SCF₃ A-819 Cl F Cl SCF₃A-820 Cl Br Cl SCF₃ A-821 Cl H Br SCF₃ A-822 Br H Br SCF₃ A-823 Br F BrSCF₃ A-824 Br Cl Br SCF₃ A-825 CF₃ H F SCF₃ A-826 CF₃ H Cl SCF₃ A-827CF₃ H Br SCF₃ A-828 CF₃ H CF₃ SCF₃ A-829 CF₃ F F SCF₃ A-830 CF₃ Cl ClSCF₃ A-831 CF₃ Br Br SCF₃ A-832 SF₅ H F SCF₃ A-833 SF₅ H Cl SCF₃ A-834SF₅ H Br SCF₃ A-835 SF₅ H CF₃ SCF₃ A-836 SF₅ H H SCF₃ A-837 CF₃ H H SCF₃A-838 Br H H SCF₃ A-839 Cl H H SCF₃ A-840 F H H SCF₃ A-841 F H F SCH₂CF₃A-842 F F F SCH₂CF₃ A-843 F Cl F SCH₂CF₃ A-844 F Br F SCH₂CF₃ A-845 F HCl SCH₂CF₃ A-846 F H Br SCH₂CF₃ A-847 Cl H Cl SCH₂CF₃ A-848 Cl Cl ClSCH₂CF₃ A-849 Cl F Cl SCH₂CF₃ A-850 Cl Br Cl SCH₂CF₃ A-851 Cl H BrSCH₂CF₃ A-852 Br H Br SCH₂CF₃ A-853 Br F Br SCH₂CF₃ A-854 Br Cl BrSCH₂CF₃ A-855 CF₃ H F SCH₂CF₃ A-856 CF₃ H Cl SCH₂CF₃ A-857 CF₃ H BrSCH₂CF₃ A-858 CF₃ H CF₃ SCH₂CF₃ A-859 CF₃ F F SCH₂CF₃ A-860 CF₃ Cl ClSCH₂CF₃ A-861 CF₃ Br Br SCH₂CF₃ A-862 SF₅ H F SCH₂CF₃ A-863 SF₅ H ClSCH₂CF₃ A-864 SF₅ H Br SCH₂CF₃ A-865 SF₅ H CF₃ SCH₂CF₃ A-866 SF₅ H HSCH₂CF₃ A-867 CF₃ H H SCH₂CF₃ A-868 Br H H SCH₂CF₃ A-869 Cl H H SCH₂CF₃A-870 F H H SCH₂CF₃ *^(c)C₃H₅ = cyclopropyl

Among the above compounds, preference is given to compounds of formulaIa.1, Ia.13, Ia.15, Ia.25, Ia.26, and Ia.27, and especially to Ia.15.

The compounds of the formula (I) can be prepared by the methods asdescribed in the below schemes or and in the synthesis descriptions ofthe working examples, or by standard methods of organic chemistry. Thesubstituents, variables and indices are as defined above for formula(I), if not otherwise specified.

Compounds of formula I can be prepared by dehydrating a compound offormula 1 as shown in scheme 1 below. X′ corresponds to a heterocyclicradical X, which however either carries a group A or a group A′, whereA′ is a precursor of A. Typical precursors of A are a halogen atom, CN,carboxy, tert-butoxycarbonyl, an acetale group, a protected aldehydegroup or —OSO₂—R^(z1), where R^(z1) is C₁-C₄-alkyl, C₁-C₄-haloalkyl orphenyl which may be substituted by 1, 2 or 3 radicals selected fromC₁-C₄-alkyl, C₁-C₄-haloalkyl C₁-C₄-alkoxy or C₁-C₄-haloalkoxy. CompoundsI′ correspond to compounds I when A′ is A (or X′ is X). Dehydrationeither occurs spontaneously or with the help of dehydrating agents, suchas molecular sieves, acid-washed molecular sieves, magnesium sulfate,sodium sulfate, silica gel, SOCl₂, POCl₃, Burgess reagent,trifluoroacetic anhydride, p-toluene sulfonic acid, anhydrous HCl orsulfuric acid. Preferably, p-toluene sulfonic acid or acid-washedmolecular sieves are used. The water formed may alternatively beremoved, e.g. by azeotropic distillation, e.g. with benzene/toluene asentrainer, e.g. using a Dean Stark trap. If necessary (i.e. if A′ is aprecursor of A), A′ is then converted into a group A.

Compounds 1 wherein R^(3b) is hydrogen can be prepared by reacting acompound 3 with an amination agent to give a compound of formula 2,which reacts spontaneously to the compound 1, as shown in scheme 2.Depending on the amination agents used, amination can the carried out ina one step reaction, wherein compound 3 reacts directly to compound 2,or as a two step reaction, wherein the SH group of compound 3 is firstoxidized to a S—Cl group, which then further reacts to a S—NH₂ group,thus giving compound 2.

Suitable amination agents for the one step reaction are for example HOSA(hydroxylamine-O-sulfonic acid), which is generally used in the presenceof a base (suitable bases being for example sodium hydrogen phosphate,potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide,sodium carbonate, potassium carbonate, sodium methanolate, triethylamineand the like), O-(diphenylphosphoryl)hydroxyl amine, which is generallyalso used in the presence of a base (suitable bases being for examplesodium hydrogen phosphate, potassium hydrogen phosphate, sodiumhydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,sodium methanolate, triethylamine and the like),2,4-dinitrophenylhydroxyl amine, O-mesitylensulfonylhydroxylamine and2-oxa-1-azaspiro[2.5]octane, among which HOSA andO-(diphenylphosphoryl)hydroxyl amine are preferred. The amination isgenerally carried out in a solvent, suitable solvents being for examplechlorinated alkanes, such as methylene chloride or chloroform, aromaticsolvents, such as benzene, toluene, the xylenes, chlorobenzene ordichlorobenzene, and ethers, such as diethylether, dipropylether, methyltert-butylether, methyl isobutylether, ethylenegylcol dimethylether,tetrahydrofuran (THF) or dioxane and the like. The reaction is suitablycarried out low temperature, e.g. at from −100 to 0° C. or −78 to 0° C.Generally, the compound 3 is dispersed in a solvent and cooled to thedesired temperature and the base is added followed by the aminationagent, or the amination agent is added followed by the base, or base andamination agent are added simultaneously. HOSA is suitably used incombination with an amine base, such as triethylamine. In this case, itis preferred to cool compound 3 to −30 to 0° C., preferably −20 to −10°C., to add the amine base at this temperature and then HOSA and keep thereaction at approximately −10 to 0° C.

Alternatively, O-(diphenylphosphoryl)hydroxyl amine can be used incombination with a base, e.g. with an inorganic base, such as sodiumhydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide,potassium hydroxide, sodium carbonate or potassium carbonate andspecifically sodium hydrogen phosphate. In this case, it is suitable tocool compound 3 to −80 to −30° C., especially −80 to −70° C., to add thebase at this temperature and then O-(diphenylphosphoryl)hydroxyl amineand keep the reaction at approximately 0° C. to room temperature.

In the two step reaction, the compound 3 is first reacted with achlorination agent which converts the SH group into an S—Cl group.Suitable chlorination agents are for example sulfurylchloride, N-chlorosuccinimide (NCS), sodium hypochlorite, monochloroamine (NH₂Cl) orchlorine, which is preferably used in the presence of FeCl₃. Thechlorination can be carried out in analogy to the method described inSynthesis 1987, 1987, 683-688, Tetrahedron 66(36), 2010, 7279-7287, J.Org. Chem. 59(4), 1994, 914-921, J. Org. Chem. 63, 1998, 4878-4888 or J.Chem Soc. 1938, 2114-2117. The chlorination is generally carried out ina solvent. Suitable solvents are for example ethers, such asdiethylether, dipropylether, methyl tert-butylether, methylisobutylether, ethylenegylcol dimethylether, tetrahydrofuran or dioxane.The reaction temperature can vary over wide ranges and is generally from0° C. to the boiling point of the reaction mixture (if a solvent isused). The chlorinated compound is then reacted without isolation withammonia or ammonium hydroxide. If anhydrous ammonia is used, thereaction is generally carried out at from −78 to −33° C. If aqueousammonia or ammonium hydroxide is used, the reaction can also be carriedout at higher temperatures, such as 0 to 25° C. The reaction isgenerally carried out in a solvent. Suitable solvents are for examplethe above-listed ethers, among which the water-miscible ethers, such asTHF and dioxane, are preferred. In general, the chlorinated compound isdissolved in a solvent to which ammonia or ammonium hydroxide is added.The reaction can be carried out as described, for example, in Synthesis,1987, 8, 683-688. The chlorination/amination can also be carried as aone pot reaction. For example, the thiol 3 is reacted simultaneouslywith a chlorinating agent (such as NCS or aqueous sodium hypochlorite)and anhydrous or aqueous ammonia in ethereal solvents (such as THF orEt₂O) or water. Preferred is the reaction with NCS in a mixture of THFand anhydrous liquid ammonia at −33° C. For instance, a solution of thethiol 3 in THF is added to a solution of NCS (N-chlorosuccinimide) inTHF/liquid ammonia at −78° C. The solution is warmed to −30° C. andstirred until the ammonia has evaporated. Alternatively, at 0° C., asolution of the sodium thiolate (NaSR) in water is added to a mixture ofaqueous ammonia (25%) and aqueous sodium hypochlorite (1 N). The one potchlorination/amination reaction can be carried out as described, forexample, in Tetrahedron 2010, 66, 7279-7287 or in J. Org. Chem. 1994,59, 914-921.

Compound 2 can virtually not be isolated as it generally reactsspontaneously in a ring-closing reaction to compound 1.

The compound of formula 3 can be prepared by reacting a compound offormula 4

with a sulfur source. Suitable sulfur sources are for example H₂S, metalhydrogen sulfides, such as NaSH or KSH, metal sulfides, such as Na₂S,K₂S Li₂S, Cu₂S, MgS, CaS, CuS, FeS and the like, ammonium sulfide[(NH₄)₂S], tetraalkylammonium sulfides (R₄NSH), such astetramethylammonium sulfide, tetraethylammonium sulfide,tetrapropylammonium sulfide and the like, or bistrimethylsilyl sulfide.H₂S as a sulfur source is generally used in the presence of a base, suchas Na₂CO₃, K₂CO₃, Cs₂CO₃, sodium acetate, potassium acetate, cesiumacetate, amines, such as diethylamine, dipropylamine, triethylamine,diisopropylethylamine and the like, or basic nitrogen-containingheterocycles, such as pyrrolidine, piperidine, piperazine, pyridine,lutidine and the like. Alternatively, H₂S as a sulfur source can be usedin the presence of a Lewis acid, such as AlCl₃ or FeCl₃. The reaction ofcompound 4 with a sulfur source is generally carried out in a solvent,suitable solvents being for example chlorinated alkanes, such asmethylene chloride or chloroform, and aromatic solvents, such asbenzene, toluene, the xylenes, chlorobenzene or dichlorobenzene. Thereaction temperature can vary over a wide range, such as −78° C. to roomtemperature. In general, compound 4 is dissolved in a solvent,optionally cooled, then the base (if used) and subsequently the sulfursource is added. The compound 4 can alternatively be reacted with asulfur source which provides a compound 3 which is protected at thethiol group SH by a protective group (S-PG). This is advantageous ifcompound 3 is for example subjected to harsher purification conditionsor is derivatized, e.g. for converting the precursor group A′ into agroup A or for modifying group A′ at this stage. Moreover, purificationof the protected product is easier. Suitable sulfuration reagents whichgive such protected thiols are for example thiourea (NH₂—C(═S)—NH₂),optionally substituted benzyl thiols, such as benzylthiol, o- orp-methoxy-benzylthiol, o- or p-hydroxybenzylthiol, o- orp-acetoxybenzylthiol, o- or p-nitrobenzylthiol or2,4,6-trimethylbenzylthiol, pyridin-4-yl-methylthiol,quinolin-2-yl-methylthiol, benzyl metal sulfides, such as sodiumbenzyl-sulfide, phenylthiol, 2,4-dinitrophenylthiol, tritylthiol,tert-butylthiol, compounds of formula R—C(═O)—NH—CH₃—SH, wherein R ismethyl, tert-butyl, allyl, phenyl or benzyl,2-trimethylsilanyl-ethanethiol, 2-(2,4-dinitrophenyl)-ethanethiol,2-phenylsulfonyl-ethanethiol, acylated thiols, such asmethylcarbonylthiol or phenylcarbonylthiol, and thiocarbamatesR—NH—C(═O)—SH, wherein R is e.g. methyl or ethyl. The benzyl and alkylthiols are generally used in the presence of a base, such as sodiumhydroxide, potassium hydroxide, sodium phosphate, potassium phosphate,sodium hydrogenphosphate, potassium hydrogenphosphate, sodium carbonate,potassium carbonate, caesium carbonate, sodium hydride, potassiumhydride, lithium diisopropyl amide (LDA), sodium methanolate, sodiumethanolate, potassium tert-butoxide, aqueous sodium tetraborate,n-butyllithium, tert-butylithium, tetrabutylammoniumfluoride (TBAF),NaHMDS and the like, or in the presence of a Lewis or Bronsted acid,such as FeCl₃, Zn(ClO₄)₂, Cu(BF₄)₂, HBF₄ or HClO₄. The reaction isgenerally carried out in a solvent, suitable solvents being for examplechlorinated alkanes, such as methylene chloride or chloroform, andethers, such as diethylether, dipropylether, methyl tert-butylether,methyl isobutylether, ethylenegylcol dimethylether, tetrahydrofuran(THF) or dioxane and the like. The reaction temperature can vary over awide range, such as from −25° C. to the boiling point of the reactionmixture. The acylated thiols can be reacted neat or in a solvent,suitable solvents being for example chlorinated alkanes, such asmethylene chloride or chloroform, and ethers, such as diethylether,dipropylether, methyl tert-butylether, methyl isobutylether,ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane and thelike. They can be used with or without a base. The S-protected compound3 can then be deprotected to the free thiol 3 under conditions generallyknown for the respective protective group, such as described, forexample, in Peter G. M. Wuts, Theodora Greene, Protective Groups inOrganic Synthesis, 4th edition, John Wiley & Sons, Inc., 2007, Chapter6.

Compound 4 can be prepared in analogy to the method described inEP-A-2172462.

Compounds 1 (in which R^(3b) is not necessarily hydrogen) can beprepared alternatively by reacting a compound of formula 6 with anamination agent to a compound of formula 5, which reacts spontaneouslyto the compound 1, as shown in scheme 3. The reaction can be carried outin analogy to that of compounds 3 and 2.

The compound of formula 6 can be obtained by reacting a compound offormula 7 with a compound of formula 8.

The reaction is preferably carried out as a Mukaiyama aldol reaction. Tothis purpose, the trialklysilyl-enolate derivative of 8 is reacted with7 in the presence of a Lewis acid, such as TiCl₄ or BF₃[O(C₂H₅)₂].Alternatively, the reaction can be carried out in the presence of astrong base, such as lithium diisopropylamide (LDA), sodiumbistrimethylsilylamide (sodium hexamethyldisilazide; NaHMDS) and amines,such as triethylamine, tripropylamine or diisopropylethylamine. Thereaction is generally carried out in a solvent. If a lithium or sodiumbase is used, the solvent is suitably an ether, such as diethylether,dipropylether, methyl tert-butylether, methyl isobutylether,ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane and thelike. Suitable reaction temperatures range from −78 to 25° C. If anamine base is used, the solvent is suitably an ether, such asdiethylether, dipropylether, methyl tert-butylether, methylisobutylether, ethylenegylcol dimethylether, tetrahydrofuran (THF) ordioxane, or an alkane, such as pentane, hexane or heptane. Suitablereaction temperatures range from 25 to 100° C.

The compound of formula 7 can be obtained by reacting a compound offormula 9 with a sulfuration agent, such as Lawesson's reagent or P₂S₅.

The reaction is generally carried out in a solvent, suitable solventsbeing for example aromatic solvents, such as benzene, toluene, thexylenes, chlorobenzene or dichlorobenzene, ethers, such as diethylether,dipropylether, methyl tert-butylether, methyl isobutylether,ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane, andhexamethyl phosphoric acid triamide (HMPA). The reaction is generallycarried out at a temperature of from 25° C. to the boiling point of thereaction mixture.

Compounds of formula I wherein R¹ is CF₃ can moreover be prepared byreacting a compound of formula 10 with a fluorinating agent and, ifnecessary (i.e. if A′ is a precursor of A), converting the group A′ intoa group A.

Suitable fluorinating agents are, for example, SF₄, preferably incombination with HF or BF₃[O(C₂H₅)₂], phenylsulfur trifluoride (Ph-SF₃),preferably in combination with HF and pyridine,4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (“Fluoled”), andbis(2-methoxyethyl)aminosulfur trifluoride [(CH₃OCH₂CH₂)₂NSF₃]. Amongthese, preference is given to SF₄ in combination with HF. If SF₄ incombination with HF is used, the reaction is carried out neat, i.e.without any further solvent. The reaction is generally carried out underelevated pressure stemming from the reactants, e.g. at a pressure offrom 2 to 10 bar, preferably from 5 to 8 bar. The reaction temperaturecan vary over wide ranges, such as from 25 to 120° C., preferably from60 to 100° C.

Alternatively, fluorination can be carried out by a two step method, inwhich the carboxyl group on the isothiazoline ring is first convertedinto a CCl₃ group, and this is subsequently fluorinated to the CF₃group. The conversion of the COOH group to the CCl₃ group is preferablycarried out by reacting the compound VI with PCl₅ and phenyl-phosphoroxydichloride (Ph-P(═O)Cl₂). The reaction can be carried out neat, i.e.without any further solvent. Suitably, the reaction is carried out atelevated temperatures, for example at from 50° C. to reflux andpreferably at reflux. Fluorination agents for converting the CCl₃ groupinto a CF₃ group are those mentioned above, and further HF and HF incombination with SbCl₅ and HF in combination with Cl₂ and SbF₃. Thereaction can be carried out neat, i.e. without any further solvent. Thereaction temperature can vary over wide ranges, for examples from 25 to300° C., preferably from 50 to 200° C. and in particular from 80 to 120°C. If the fluorination agent is HF or HF in combination with a furtheragent, the reaction generally takes place at the pressure stemming fromHF and ranging generally from 2 to 10 bar, preferably from 5 to 8 bar.

The compound of formula 10 is preferably obtained by hydrolyzing acompound of formula 11, wherein R is C₁-C₄-alkyl.

Hydrolysis can be carried out by any suitable means known forhydrolyzing ester groups, such as acidic conditions, e.g. usinghydrochloric acid, hydrobromic acid, sulfuric acid, trifluoroaceticacid, etc., or by basic conditions, e.g. using an alkali metalhydroxide, such as LiOH, NaOH or KOH, or an alkali metal carbonate, suchas sodium or potassium carbonate.

The compound of formula 11 can in turn be obtained by reacting acompound 12 with a compound 13

The reaction is carried out at elevated temperature, e.g. at from 90 to200° C., preferably from 100 to 180° C. and in particular from 120 to160° C., e.g. at about 140° C.

The compound of formula 12 can in turn be obtained by reacting acompound 15 with a compound 16

The reaction is generally carried out in a solvent, suitable solventsbeing for example aromatic solvents, such as benzene, toluene, thexylenes, chlorobenzene and dichlorobenzene. The reaction temperature ispreferably from 80 to 140° C., more preferably from 100 to 120° C.

Compounds of formula I wherein however R¹ is CF₃ can moreover beprepared by reacting a compound of formula 12 as defined above with acompound of formula 14 and, if necessary, converting the group A′ into agroup A.

The reaction is carried out at elevated temperature, e.g. at from 90 to200° C., preferably from 100 to 180° C. and in particular from 120 to160° C., e.g. at about 140° C.

Compounds I′, in which A′ is a precursor of A can be converted as shownbelow into the different groups A¹ to A³.

Compounds I′, in which A′ is Cl, Br, I or —OSO₂—R^(z1), where R^(z1) isas defined above, can be converted to compounds I wherein A is a groupA¹, wherein A¹ is an imino group —C(═NR⁶)R⁸, by reaction with carbonmonoxide and a hydride source, such as triethylsilane, in the presenceof a transition metal complex catalyst, preferably a palladium catalyst,to a carbonyl compound 17. This reaction converts the starting group A′into a carbonyl group —C(═O)H.

The aldehyde 17 can also be obtained by reducing the ester 20 (seebelow; R=C₁-C₄-alkyl) with diisobutylaluminium hydride (DIBAL-H) eitherdirectly to the aldehyde 17 or via the corresponding alcohol, which isthen oxidized to the aldehyde.

For obtaining compounds in which R⁸ in the imino group is H, suchcarbonyl compounds 17 are then reacted with an amine (derivative) NH₂R⁶.Alternatively, the compound I′, in which A′ is Cl, Br, I or—OSO₂—R^(z1), where R^(z1) is as defined above, can be reacted in a onepot reaction with carbon monoxide and hydrogen in the presence of atransition metal complex catalyst and the amine NH₂R⁶.

For obtaining compounds in which R⁸ in the imino group is not H, thecarbonyl compounds are reacted with a Grignard reagent R⁸—MgHaI, whereHal is Cl, Br or I, or an organolithium compound R⁸—Li to obtain analcohol of formula 18, which is then oxidized to a carbonyl compound ofthe formula 19, as shown in scheme 4. This is then reacted with an amineNH₂R⁶ to the respective imine compound.

These reactions can be carried out in analogy to the methods describedin PCT/EP 2011/060388 or in WO 2010/072781 and the references citedtherein, especially WO 2006135763, Fattorusso et al, J. Med. Chem. 2008,51, 1333-1343 and WO 2008/122375.

Compounds I wherein A is a group A¹, wherein A¹ is —S(O)_(n)R⁹ or—N(R⁵)R⁶, can for example be prepared by reacting a compound I′ whereinA′ is Cl, Br or I in a Ullmann-type reaction with an amine NHR⁵R⁶ or athiol SHR⁹ in the presence of a Cu(I) catalyst. To obtain a compoundwherein A¹ is —S(O)_(n)R⁹ wherein n is not 0 the thiol can then beoxidized, e.g. with hydrogen peroxide. Amine and thiol groups canfurther be introduced in a Buchwald-Hartwig reaction by reacting acompound I′ wherein A′ is Cl, Br or I with an amine NHR⁵R⁶ or a thiolHSR⁹ in the presence of a palladium catalyst, such as PdCl₂(dppf) in thepresence of a base, such as cesium carbonate or N,N-diisopropylethylamine, and optionally in the presence of a phosphine ligand, such asXantphos (“4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene”).

Thioethers (A¹=—SR⁹) can further be introduced by reacting a compound I′wherein A′ is F in an S_(N)Ar reaction (nucleophilic aromaticsubstitution reaction) with a thiol HSR⁹ in the presence of a base, suchas potassium carbonate (K₂CO₃), or with a thiolate (e.g. NaSR⁹).

Compounds I wherein A is a group A², wherein W is O can be prepared byreacting a compound I′ wherein A′ is Cl, Br, I or triflate with carbonmonoxide in the presence of a palladium catalyst and an alcohol ROH,wherein R is C₁-C₄-alkyl, to a compound of formula 20. Suitablepalladium catalysts are for example those described in PCT/EP2011/060388.

This ester is then hydrolyzed to the respective carboxylic acid, whichis the reacted under standard amidation conditions with an amine NHR⁵R⁶.Hydrolyzation can be carried out under standard conditions, e.g. underacidic conditions using for example hydrochloric acid, sulfuric acid ortrifluoroacetic acid, or under basic conditions using for example analkali metal hydroxide, such as LiOH, NaOH or KOH. Amidation ispreferably carried out by activation of the carboxylic acids withoxalylchloride [(COCl)₂] or thionylchloride (SOCl₂) to the respectiveacid chlorides, followed by reaction with an amine NHR⁵R⁶.Alternatively, amidation is carried out in the presence of a couplingreagent. Suitable coupling reagent (activators) are well known and arefor instance selected from carbodiimides, such as DCC(dicyclohexylcarbodiimide) and DCI (diisopropylcarbodiimide),benzotriazol derivatives, such as HATU(O-(7-azabenzotriazol-1-yl)N,N,N′,N′-tetramethyluroniumhexafluorophosphate), HBTU((0-benzotriazol-1-yl)N,N,N′,N′-tetramethyluronium hexafluorophosphate)and HCTU (1H-benzotriazolium-1-[bis(dimethylamino)methylene]-5-chlorotetrafluoroborate) and phosphonium-derived activators, such as BOP((benzotriazol-1-yloxy)-tris(dimethylamino)phosphoniumhexafluorophosphate), Py-BOP((benzotriazol-1-yloxy)-tripyrrolidinphosphonium hexafluorophosphate)and Py-BrOP (bromotripyrrolidinphosphonium hexafluorophosphate).

Generally, the activator is used in excess. The benzotriazol andphosphonium coupling reagents are generally used in a basic medium.

Compounds I wherein A is a group A², wherein W is S, can be prepared byreacting the corresponding oxo-compound (W is O) with Lawesson's reagent(CAS 19172-47-5), see for example Jesberger et al., Synthesis, 2003,1929-1958 and references therein. Solvents such as HMPA or THF at anelevated temperature such as 60° C. to 100° C. can be used. Preferredreaction conditions are THF at 65° C.

Compounds I wherein A is a group A³, wherein R^(7a) and R^(7b) arehydrogen, can be prepared by reducing a compound 20 or 17 for examplewith LAH (lithium aluminium hydride) or DIBAL-H (diisobutyl aluminiumhydride) to a compound 21.

This is then reacted in an SN reaction with an amine NHR⁵R⁶. For thispurpose, the OH group can first be converted into a better leavinggroup, e.g. into a sulfonate (for example mesylate, tosylate or atriflate group). If R⁶ is a group —C(O)R⁸, it is alternatively possibleto react compound 21 with an amine NH₂R⁵ and react then the resultingbenzylic amine with an acid R⁸—COOH or a derivative thereof, such as itsacid chloride R³—COCl, in an amidation reaction.

Compounds I wherein A is a group A³, wherein R^(7a) is optionallysubstituted alkyl or optionally substituted cycloalkyl and R^(7b) ishydrogen, can be prepared by subjecting a ketone 19, in which R⁸corresponds to R^(7a) which is optionally substituted C₁-C₆-alkyl oroptionally substituted C₃-C₈-cycloalkyl, to a reductive amination tofurnish compounds 22. Typical conditions for the reductive aminationare: Reacting ketone 19 with an amine H₂NR⁵ to yield the correspondingimine which is reduced to amine 22 with a reducing agent reagent such asNa(CN)BH₃. The reaction from ketone 19 to amine 22 may also be carriedout as a one pot procedure.

For obtaining compounds in which R^(7a) and R^(4b) are optionallysubstituted alkyl, optionally substituted cycloalkyl, optionallysubstituted alkenyl or optionally substituted alkynyl, carbonylcompounds such as 19, in which R⁸ corresponds to R^(7a) which isoptionally substituted C₁-C₆-alkyl, optionally substitutedC₃-C₈-cycloalkyl, optionally substituted C₂-C₆-alkenyl or optionallysubstituted C₂-C₆-alkynyl, is reacted with a Grignard reagentR^(7b)-MgHaI, where Hal is Cl, Br or I, or an organolithium compoundR^(7b)—Li, where R^(4b) is optionally substituted C₁-C₆-alkyl,optionally substituted C₃-C₈-cycloalkyl, optionally substitutedC₂-C₆-alkenyl or optionally substituted C₂-C₆-alkynyl, to obtain analcohol of formula 23.

Alcohol 23 can then be converted into amine 24 via the correspondingazide, as described, for example, in Organic Letters, 2001, 3(20),3145-3148.

If desired, this can be converted into compounds I wherein R⁵ and R⁶ aredifferent from hydrogen, for example by standard alkylation or acylationreactions.

Compounds I wherein A is a group A³, wherein R^(7a) is optionallysubstituted alkyl, alkenyl, alkynyl, cycloalkyl or CN and R^(7b) ishydrogen, can be prepared by converting an aldehyde 17 into an imine 25by reaction with an amine derivative NH₂R⁶, wherein R⁶ is tert-butylsulfinyl, or, for preparing a compound with R^(7a)═CN, tosylate.

This imine is then reacted with a compound H—R^(7a) in an additionreaction under conditions as described for example in J. Am. Chem. Soc.2009, 3850-3851 and the references cited therein, or, for introducing CNas a group R^(7a), Chemistry—A European Journal 2009, 15, 11642-11659.

Compounds I wherein A is a group A³, wherein both R^(7a) and R^(7b) areoptionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or CN, can beprepared analogously by converting a ketone 19, wherein R⁸ is has themeaning desired for R^(7b) and is optionally substituted alkyl, alkenyl,alkynyl, cycloalkyl or CN, into an imine by reaction with an aminederivative NH₂R⁶, wherein R⁶ is tert-butyl sulfinyl, or, for preparing acompound 26 with R^(7a)═CN, tosylate.

This imine is then reacted with a compound H—R^(7a) in an additionreaction under conditions as described for example in J. Org. Chem 2002,67, 7819-7832 and the references cited therein, or, for introducing CNas a group R^(7a), Chemistry—A European Journal 2009, 15, 11642-11659.If desired, R⁶ can then be removed to yield an amino group NH₂.

Compounds I wherein A is A⁴ can be prepared by standard ring couplingreactions. For example, compounds, wherein A⁴ is an N-bound heterocyclicring can be prepared by reacting a compound I′ wherein A′ is Cl, Br or Iwith the respective ring A⁴-H (H being on the nitrogen ring atom to becoupled) under Ullmann coupling conditions, such as described, forexample, in WO 2007/075459. Typically, copper(I) iodide or copper(I)oxide and a ligand such as 1,2-cyclohexyldiamine is used, see forexample Kanemasa et al., European Journal of Organic Chemistry, 2004,695-709. If A′ is F, the reaction is typically run in a polar aproticsolvent such as N,N-dimethylformamide, N,N-dimethylacetamide orN-methylpyrrolidone, and in the presence of an inorganic base such assodium, potassium or cesium carbonate.

Compounds, wherein A⁴ is a C-bound heterocyclic ring can be prepared byreacting a compound I′ wherein A′ is Br or I with the boronic acid ofthe respective ring A⁴-B(OH)₂ or the boronate ester of the respectivering A⁴-B(OR₂) under Suzuki reaction conditions via Pd-catalyzed crosscoupling, such as described, for example, in WO 2007/075459. A typicalcatalyst is tetrakis(triphenylphosphine)palladium(0). Solvents such astetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable.The boronic acids A⁴-B(OH)₂ are either commercially available or can beprepared by known methods. Other methods for introduction of theheterocyclic groups A⁴ are the Heck, Stille, Kumada and Buchwald-Hartwigcoupling procedures; see for example Tetrahedron, 2004, 60, 8991-9016.

As a rule, the compounds of formula (I) including their stereoisomers,salts, and N-oxides, and their precursors in the synthesis process, canbe prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared byderivatization of other compounds (I) or the respective precursor or bycustomary modifications of the synthesis routes described. For example,in individual cases, certain compounds of formula (I) can advantageouslybe prepared from other compounds of formula (I) by derivatization, e.g.by ester hydrolysis, amidation, esterification, ether cleavage,olefination, reduction, oxidation and the like, or by customarymodifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for exampleby mixing with water, separating the phases, and, if appropriate,purifying the crude products by chromatography, for example on aluminaor on silica gel. Some of the intermediates and end products may beobtained in the form of colorless or pale brown viscous oils which arefreed or purified from volatile components under reduced pressure and atmoderately elevated temperature. If the intermediates and end productsare obtained as solids, they may be purified by recrystallization ortrituration.

Due to their excellent activity, the compounds of the present inventionmay be used for controlling invertebrate pests.

Accordingly, the present invention also provides a method forcontrolling invertebrate pests which method comprises treating thepests, their food supply, their habitat or their breeding ground or acultivated plant, plant propagation materials (such as seed), soil,area, material or environment in which the pests are growing or maygrow, or the materials, cultivated plants, plant propagation materials(such as seed), soils, surfaces or spaces to be protected from pestattack or infestation with a pesticidally effective amount of a compoundof the present invention or a composition as defined above. Theinvention also relates to the use of a compound of the invention, of astereoisomer and/or of an agriculturally or veterinarily acceptable saltthereof for combating invertebrate pests

Preferably, the method of the invention serves for protecting plantpropagation material (such as seed) and the plant which grows therefromfrom invertebrate pest attack or infestation and comprises treating theplant propagation material (such as seed) with a pesticidally effectiveamount of a compound of the present invention as defined above or with apesticidally effective amount of an agricultural composition as definedabove and below. The method of the invention is not limited to theprotection of the “substrate” (plant, plant propagation materials, soilmaterial etc.) which has been treated according to the invention, butalso has a preventive effect, thus, for example, according protection toa plant which grows from a treated plant propagation materials (such asseed), the plant itself not having been treated.

Alternatively preferably, the method of the invention serves forprotecting plants from attack or infestation by invertebrate pests,which method comprises treating the plants with a pesticidally effectiveamount of at least one compound of the invention, a stereoisomer thereofand/or at least one agriculturally acceptable salt thereof.

In the sense of the present invention, “invertebrate pests” arepreferably selected from arthropods and nematodes, more preferably fromharmful insects, arachnids and nematodes, and even more preferably frominsects, acarids and nematodes. In the sense of the present invention,“invertebrate pests” are most preferably insects.

The invention further provides an agricultural composition for combatinginvertebrate pests, which comprises such an amount of at least onecompound according to the invention and at least one inert liquid and/orsolid agronomically acceptable carrier that has a pesticidal action and,if desired, at least one surfactant.

Such a composition may comprise a single active compound of the presentinvention or a mixture of several active compounds of the presentinvention. The composition according to the present invention maycomprise an individual isomer or mixtures of isomers or a salt as wellas individual tautomers or mixtures of tautomers.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are in particular suitable for efficientlycontrolling arthropodal pests such as arachnids, myriapedes and insectsas well as nematodes. They are especially suitable for efficientlycombating or controlling the following pests:

insects from the order of the lepidopterans (Lepidoptera), for exampleAcronicta major, Adoxophyes orana, Aedia leucomelas, Agrotis spp. suchas Agrotis fucosa, Agrotis segetum, Agrotis ipsilon; Alabama argillacea,Anticarsia gemmatalis, Anticarsia spp., Argyresthia conjugella,Autographa gamma, Barathra brassicae, Bucculatrix thurberiella, Bupaluspiniarius, Cacoecia murinana, Cacoecia podana, Capua reticulana,Carpocapsa pomonella, Cheimatobia brumata, Chilo spp. such as Chilosuppressalis; Choristoneura fumiferana, Choristoneura occidentalis,Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cydiapomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella,Earias insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestiakuehniella, Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp.,Evetria bouliana, Feltia spp. such as Feltia subterranean; Galleriamellonella, Grapholitha funebrana, Grapholitha molesta, Helicoverpa spp.such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such asHeliothis armigera, Heliothis virescens, Heliothis zea; Hellula undalis,Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima,Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Keiferialycopersicella, Lambdina fiscellaria, Laphygma spp. such as Laphygmaexigua; Leucoptera coffeella, Leucoptera scitella, Lithocolletisblancardella, Lithophane antennata, Lobesia botrana, Loxagrotisalbicosta, Loxostege sticticalis, Lymantria spp. such as Lymantriadispar, Lymantria monacha; Lyonetia clerkella, Malacosoma neustria,Mamestra spp. such as Mamestra brassicae; Mocis repanda, Mythimnaseparata, Orgyia pseudotsugata, Oria spp., Ostrinia spp. such asOstrinia nubilalis; Oulema oryzae, Panolis flammea, Pectinophora spp.such as Pectinophora gossypiella; Peridroma saucia, Phalera bucephala,Phthorimaea spp. such as Phthorimaea operculella; Phyllocnistiscitrella, Pieris spp. such as Pieris brassicae, Pieris rapae; Plathypenascabra, Plutella maculipennis, Plutella xylostella, Prodenia spp.,Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rhyacioniafrustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothispilleriana, Spodoptera spp. such as Spodoptera frugiperda, Spodopteralittoralis, Spodoptera litura; Thaumatopoea pityocampa, Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp. such as Trichoplusia ni; Tuta absoluta, and Zeirapheracanadensis,beetles (Coleoptera), for example Acanthoscehdes obtectus, Adoretusspp., Agelastica alni, Agrilus sinuatus, Agriotes spp. such as Agriotesfuscicollis, Agriotes lineatus, Agriotes obscurus; Amphimallussolstitialis, Anisandrus dispar, Anobium punctatum, Anomala rufocuprea,Anoplophora spp. such as Anoplophora glabripennis; Anthonomus spp. suchas Anthonomus grandis, Anthonomus pomorum; Anthrenus spp., Aphthonaeuphoridae, Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such asAtomaria linearis; Attagenus spp., Aulacophora femoralis, Blastophaguspiniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such asBruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae,Callosobruchus chinensis, Cassida nebulosa, Cerotoma trifurcata, Cetoniaaurata, Ceuthorhynchus spp. such as Ceuthorrhynchus assimilis,Ceuthorrhynchus napi; Chaetocnema tibialis, Cleonus mendicus, Conoderusspp. such as Conoderus vespertinus; Cosmopolites spp., Costelytrazea-landica, Crioceris asparagi, Cryptorhynchus lapathi, Ctenicera ssp.such as Ctenicera destructor; Curculio spp., Dectes texanus, Dermestesspp., Diabrotica spp. such as Diabrotica 12-punctata Diabroticaspeciosa, Diabrotica longicornis, Diabrotica semi-punctata, Diabroticavirgifera; Epilachna spp. such as Epilachna varivestis, Epilachnavigintioctomaculata; Epitrix spp. such as Epitrix hirtipennis;Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides,Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupesbajulus, Hypera brunneipennis, Hypera postica, Hypothenemus spp., Ipstypographus, Lachnosterna consanguinea, Lema bilineata, Lema melanopus,Leptinotarsa spp. such as Leptinotarsa decemlineata; Limoniuscalifornicus, Lissorhoptrus oryzophilus, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis,Meligethes spp. such as Meligethes aeneus; Melolontha hippocastani,Melolontha melolontha, Migdolus spp., Monochamus spp. such as Monochamusalternatus; Naupactus xanthographus, Niptus hololeucus, Oryctesrhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus,Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema oryzae, Oxycetoniajucunda, Phaedon cochleariae, Phyllobius pyri, Phyllopertha horticola,Phyllophaga spp., Phyllotreta spp. such as Phyllotreta chrysocephala,Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp.,Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psylliodeschrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica,Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophiluszeamais; Sphenophorus spp. such as Sphenophorus levis; Sternechus spp.such as Sternechus subsignatus; Symphyletes spp., Tenebrio molitor,Tribolium spp. such as Tribolium castaneum; Trogoderma spp., Tychiusspp., Xylotrechus spp., and Zabrus spp. such as Zabrus tenebrioides,flies, mosquitoes (Diptera), e.g. Aedes spp. such as Aedes aegypti,Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp. suchas Anopheles albimanus, Anopheles crucians, Anopheles freeborni,Anopheles gambiae, Anopheles leucosphyrus, Anopheles maculipennis,Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibiohortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitiscapitata, Ceratitis capitata, Chrysomyia spp. such as Chrysomyabezziana, Chrysomya hominivorax, Chrysomya macellaria; Chrysopsatlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. suchas Cochliomyia hominivorax; Contarinia spp. such as Contariniasorghicola; Cordylobia anthropophaga, Culex spp. such as Culexnigripalpus, Culex pipiens, Culex quinquefasciatus, Culex tarsalis,Culex tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culisetamelanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineurabrassicae, Delia spp. such as Delia antique, Delia coarctata, Deliaplatura, Delia radicum; Dermatobia hominis, Drosophila spp., Fannia spp.such as Fannia canicularis; Gastraphilus spp. such as Gasterophilusintestinalis; Geomyza Tripunctata, Glossina fuscipes, Glossinamorsitans, Glossina palpalis, Glossina tachinoides, Haematobia irritans,Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as Hylemyiaplatura; Hypoderma spp. such as Hypoderma lineata; Hyppobosca spp.,Leptoconops torrens, Liriomyza spp. such as Liriomyza sativae, Liriomyzatrifolii; Lucilia spp. such as Lucilia caprina, Lucilia cuprina, Luciliasericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. suchas Mayetiola destructor; Musca spp. such as Musca autumnalis, Muscadomestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyzaflorum, Oscinella spp. such as Oscinella frit; Pegomya hysocyami,Phlebotomus argentipes, Phorbia spp. such as Phorbia antiqua, Phorbiabrassicae, Phorbia coarctata; Prosimulium mixtum, Psila rosae,Psorophora columbiae, Psorophora discolor, Rhagoletis cerasi, Rhagoletispomonella, Sarcophaga spp. such as Sarcophaga haemorrhoidalis; Simuliumvittatum, Stomoxys spp. such as Stomoxys calcitrans; Tabanus spp. suchas Tabanus atratus, Tabanus bovinus, Tabanus lineola, Tabanus similis;Tannia spp., Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp.,thrips (Thysanoptera), e.g. Baliothrips biformis, Dichromothripscorbetti, Dichromothrips ssp., Enneothrips flavens, Frankliniella spp.such as Frankliniella fusca, Frankliniella occidentalis, Frankliniellatritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,Rhipiphorothrips cruentatus, Scirtothrips spp. such as Scirtothripscitri; Taeniothrips cardamoni, Thrips spp. such as Thrips oryzae, Thripspalmi, Thrips tabaci;termites (Isoptera), e.g. Calotermes flavicollis, Coptotermesformosanus, Heterotermes aureus, Heterotermes longiceps, Heterotermestenuis, Leucotermes flavipes, Odontotermes spp., Reticulitermes spp.such as Reticulitermes speratus, Reticulitermes flavipes, Reticulitermesgrassei, Reticulitermes lucifugus, Reticulitermes santonensis,Reticulitermes virginicus; Termes natalensis,cockroaches (Blattaria—Blattodea), e.g. Acheta domesticus, Blattaorientalis, Blattella asahinae, Blattella germanica, Gryllotalpa spp.,Leucophaea maderae, Locusta spp., Melanoplus spp., Periplanetaamericana, Periplaneta australasiae, Periplaneta brunnea, Periplanetafuligginosa, Periplaneta japonica,bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas(Hemiptera), e.g. Acrosternum spp. such as Acrosternum hilare;Acyrthosipon spp. such as Acyrthosiphon onobrychis, Acyrthosiphon pisum;Adelges laricis, Aeneolamia spp., Agonoscena spp., Aleurodes spp.,Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis,Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri,Aphidula nasturtii, Aphis spp. such as Aphis fabae, Aphis forbesi, Aphisgossypii, Aphis grossulariae, Aphis pomi, Aphis sambuci, Aphisschneideri, Aphis spiraecola; Arboridia apicalis, Arilus critatus,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp. such as Bemisia argentifolii, Bemisia tabaci; Blissus spp.such as Blissus leucopterus; Brachycaudus cardui, Brachycaudushelichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brachycolusspp., Brevicoryne brassicae, Calligypona marginate, Calocoris spp.,Campylomma livida, Capitophorus horni, Carneocephala fulgida, Caveleriusspp., Ceraplastes spp., Ceratovacuna lanigera, Cercopidae, Cerosiphagossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chloritaonukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila,Cimex spp. such as Cimex hemipterus, Cimex lectularius; Coccomytilushalli, Coccus spp., Creontiades dilutus, Cryptomyzus ribis, Cryptomyzusribis, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeuradesspp., Diaphorina spp., Diaspis spp., Dichelops furcatus, Diconocorishewetti, Doralis spp., Dreyfusia nordmannianae, Dreyfusia piceae,Drosicha spp., Dysaphis spp. such as Dysaphis plantaginea, Dysaphispyri, Dysaphis radicula; Dysaulacorthum pseudosolani, Dysdercus spp.such as Dysdercus cingulatus, Dysdercus intermedius; Dysmicoccus spp.,Empoasca spp. such as Empoasca fabae, Empoasca solana; Eriosoma spp.,Erythroneura spp., Eurygaster spp. such as Eurygaster integriceps;Euscelis bilobatus, Euschistus spp. such as Euschistuos heros,Euschistus impictiventris, Euschistus servus; Geococcus coffeae,Halyomorpha spp. such as Halyomorpha halys; Heliopeltis spp.,Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni,Hyperomyzus lactucae, Icerya spp., Idiocerus spp., Idioscopus spp.,Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Leptocorisaspp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as Lygushesperus, Lygus lineolaris, Lygus pratensis; Macropes excavatus,Macrosiphum spp. such as Macrosiphum rosae, Macrosiphum avenae,Macrosiphum euphorbiae; Mahanarva fimbriolata, Megacopta cribraria,Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Metcafiellaspp., Metopolophium dirhodum, Miridae spp., Monellia costalis,Monelliopsis pecanis, Myzus spp. such as Myzus ascalonicus, Myzuscerasi, Myzus persicae, Myzus varians; Nasonovia ribis-nigri,Nephotettix spp. such as Nephotettix malayanus, Nephotettix nigropictus,Nephotettix parvus, Nephotettix virescens; Nezara spp. such as Nezaraviridula; Nilaparvata lugens, Oebalus spp., Oncometopia spp., Ortheziapraelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp.,Pemphigus spp. such as Pemphigus bursarius; Pentomidae, Peregrinusmaidis, Perkinsiella saccharicida, Phenacoccus spp., Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., Piesma quadrata,Piezodorus spp. such as Piezodorus guildinii, Pinnaspis aspidistrae,Planococcus spp., Protopulvinaria pyriformis, Psallus seriatus,Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such asPseudococcus comstocki; Psylla spp. such as Psylla mall, Psylla piri;Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas,Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzusascalonicus, Rhopalosiphum spp. such as Rhopalosiphum pseudobrassicas,Rhopalosiphum insertum, Rhopalosiphum maidis, Rhopalosiphum padi;Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala,Sappaphis mali, Scaphoides titanus, Schizaphis graminum, Schizoneuralanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobionavenae, Sogata spp., Sogatella furcifera, Solubea insularis, Stephanitisnashi, Stictocephala festina, Tenalaphara malayensis, Thyanta spp. suchas Thyanta perditor; Tibraca spp., Tinocallis caryaefoliae, Tomaspisspp., Toxoptera spp. such as Toxoptera aurantii; Trialeurodes spp. suchas Trialeurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocybaspp., Unaspis spp. such as Unaspis yanonensis; and Viteus vitifolii,ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Attacapiguara, Atta cephalotes, Atta cephalotes, Atta laevigata, Attarobusta, Atta sexdens, Atta texana, Bombus spp., Camponotus floridanus,Crematogaster spp., Dasymutilla occidentalis, Diprion spp.,Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta,Hoplocampa testudinea; Lasius spp. such as Lasius niger, Linepithemahumile, Monomorium pharaonis, Paravespula germanica, Paravespulapennsylvanica, Paravespula vulgaris, Pheidole megacephala, Pogonomyrmexbarbatus, Pogonomyrmex californicus, Polistes rubiginosa, Solenopsisgeminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni,Vespa spp. such as Vespa crabro, and Vespula squamosa,crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica,Calliptamus italicus, Chortoicetes terminifera, Dociostaurus maroccanus,Gryllotalpa africana, Gryllotalpa gryllotalpa, Hieroglyphus daganensis,Kraussaria angulifera, Locusta migratoria, Locustana pardalina,Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus,Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata,Oedaleus senegalensis, Schistocerca americana, Schistocerca gregaria,Tachycines asynamorus, and Zonozerus variegatus,arachnids (Arachnida), such as acari, e.g. of the families Argasidae,Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. Amblyommaamericanum, Amblyomma variegatum, Amblyomma maculatum), Argas spp. (e.g.Argas persicus), Boophilus spp. (e.g. Boophilus annulatus, Boophilusdecoloratus, Boophilus microplus), Dermacentor silvarum, Dermacentorandersoni, Dermacentor variabilis, Hyalomma spp. (e.g. Hyalommatruncatum), Ixodes spp. (e.g. Ixodes ricinus, Ixodes rubicundus, Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus), Ornithodorus spp.(e.g. Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata),Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptesspp. (e.g. Psoroptes ovis), Rhipicephalus spp. (e.g. Rhipicephalussanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi),Rhizoglyphus spp., Sarcoptes spp. (e.g. Sarcoptes scabiei), andEriophyidae spp. such as Acaria sheldoni, Aculops spp. (e.g. Aculopspelekassi) Aculus spp. (e.g. Aculus schlechtendali), Epitrimerus pyri,Phyllocoptruta oleivora and Eriophyes spp. (e.g. Eriophyes sheldoni);Tarsonemidae spp. such as Hemitarsonemus spp., Phytonemus pallidus andPolyphagotarsonemus latus, Stenotarsonemus spp.; Tenuipalpidae spp. suchas Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp.such as Eotetranychus spp., Eutetranychus spp., Oligonychus spp.,Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus,Tetranychus telarius and Tetranychus urticae; Bryobia praetiosa,Panonychus spp. (e.g. Panonychus ulmi, Panonychus citri),Metatetranychus spp. and Oligonychus spp. (e.g. Oligonychus pratensis),Vasates lycopersici; Araneida, e.g. Latrodectus mactans, and Loxoscelesreclusa. And Acarus siro, Chorioptes spp., Scorpio maurusfleas (Siphonaptera), e.g. Ceratophyllus spp., Ctenocephalides felis,Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tungapenetrans, and Nosopsyllus fasciatus,silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobiadomestica,centipedes (Chilopoda), e.g. Geophilus spp., Scutigera spp. such asScutigera coleoptrata;millipedes (Diplopoda), e.g. Blaniulus guttulatus, Narceus spp.,Earwigs (Dermaptera), e.g. forficula auricularia,lice (Phthiraptera), e.g. Damalinia spp., Pediculus spp. such asPediculus humanus capitis, Pediculus humanus corporis; Pthirus pubis,Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis;Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopongallinae, Menacanthus stramineus and Solenopotes capillatus,Trichodectes spp.,springtails (Collembola), e.g. Onychiurus ssp. such as Onychiurusarmatus,

They are also suitable for controlling nematodes: plant parasiticnematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyneincognita, Meloidogyne javanica, and other Meloidogyne species;cyst-forming nematodes, Globodera rostochiensis and other Globoderaspecies; Heterodera avenae, Heterodera glycines, Heterodera schachtii,Heterodera trifolii, and other Heterodera species; Seed gall nematodes,Anguina species; Stem and foliar nematodes, Aphelenchoides species suchas Aphelenchoides besseyi; Sting nematodes, Belonolaimus longicaudatusand other Belonolaimus species; Pine nematodes, Bursaphelenchuslignicolus Mamiya et Kiyohara, Bursaphelenchus xylophilus and otherBursaphelenchus species; Ring nematodes, Criconema species, Criconemellaspecies, Criconemoides species, Mesocriconema species; Stem and bulbnematodes, Ditylenchus destructor, Ditylenchus dipsaci and otherDitylenchus species; Awl nematodes, Dolichodorus species; Spiralnematodes, Heliocotylenchus multicinctus and other Helicotylenchusspecies; Sheath and sheathoid nematodes, Hemicycliophora species andHemicriconemoides species; Hirshmanniella species; Lance nematodes,Hoploaimus species; false rootknot nematodes, Nacobbus species; Needlenematodes, Longidorus elongatus and other Longidorus species; Lesionnematodes, Pratylenchus brachyurus, Pratylenchus neglectus, Pratylenchuspenetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and otherPratylenchus species; Burrowing nematodes, Radopholus similis and otherRadopholus species; Reniform nematodes, Rotylenchus robustus,Rotylenchus reniformis and other Rotylenchus species; Scutellonemaspecies; Stubby root nematodes, Trichodorus primitivus and otherTrichodorus species, Paratrichodorus species; Stunt nematodes,Tylenchorhynchus claytoni, Tylenchorhynchus dubius and otherTylenchorhynchus species; Citrus nematodes, Tylenchulus species such asTylenchulus semi-penetrans; Dagger nematodes, Xiphinema species; andother plant parasitic nematode species.

Examples of further pest species which may be controlled by compounds offormula (I) include: from the class of the Bivalva, for example,Dreissena spp.; from the class of the Gastropoda, for example, Anionspp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp.,Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of thehelminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum,Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascarisspp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp.,Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria,Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus,Echinococcus multilocularis, Enterobius vermicularis, Faciola spp.,Haemonchus spp. such as Haemonchus contortus; Heterakis spp.,Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp.,Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagiaspp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni,Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taeniasolium, Trichinella spiralis, Trichinella nativa, Trichinella britovi,Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp.,Trichuris trichiura, Wuchereria bancrofti; from the order of theIsopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellioscaber; from the order of the Symphyla, for example, Scutigerellaimmaculata;

Further examples of pest species which may be controlled by compounds offormula (I) include: Anisoplia austriaca, Apamea spp., Austroascaviridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp.,Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chiloindicus, Chilo polychrysus, Chortiocetes terminifera, Cnaphalocrocimedinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp.,Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulusmaidis, Deraceras reticulaturn, Diatrea saccharalis, Dichelops furcatus,Dicladispa armigera, Diloboderus spp. such as Diloboderus abderus;Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Globitermessulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor,Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta,Leptocorsia oratorius, Liogenys fuscus, Lucillia spp., Lyogenys fuscus,Mahanarva spp., Maladera matrida, Marasmia spp., Mastotermes spp.,Mealybugs, Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocislatipes, Murgantia spp., Mythemina separata, Neocapritermes opacus,Neocapritermes parvus, Neomegalotomus spp., Neotermes spp., Nymphuladepunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae;Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata,Procornitermes ssp, Procornitermes triacifer, Psylloides spp.,Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocorisspp., Scirpophaga spp. such as Scirpophaga incertulas, Scirpophagainnotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp.such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata,Spissistilus spp., Stalk borer, Stenchaetothrips biformis,Steneotarsonemus spinki, Sylepta derogata, Telehin licus,Trichostrongylus spp.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are particularly useful for controllinginsects, preferably sucking or piercing and chewing and biting insectssuch as insects from the genera Lepidoptera, Coleoptera and Hemiptera,in particular Lepidoptera, Coleoptera and true bugs.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are moreover useful for controlling insectsof the orders Thysanoptera, Diptera (especially flies, mosquitos),Hymenoptera (especially ants) and Isoptera (especially termites.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are particularly useful for controllinginsects of the orders Lepidoptera and Coleoptera.

The invention also relates to agrochemical compositions comprising anauxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a pesticidally effective amount ofa compound I. The term “effective amount” denotes an amount of thecomposition or of the compounds I, which is sufficient for controllingharmful fungi on cultivated plants or in the protection of materials andwhich does not result in a substantial damage to the treated plants.Such an amount can vary in a broad range and is dependent on variousfactors, such as the species to be controlled, the treated cultivatedplant or material, the climatic conditions and the specific compound Iused.

The compounds I, their N-oxides and salts can be converted intocustomary types of agrochemical compositions, e.g. solutions, emulsions,suspensions, dusts, powders, pastes, granules, pressings, capsules, andmixtures thereof. Examples for composition types are suspensions (e.g.SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW,EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powdersor dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT),granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN),as well as gel formulations for the treatment of plant propagationmaterials such as seeds (e.g. GF). These and further compositions typesare defined in the “Catalogue of pesticide formulation types andinternational coding system”, Technical Monograph No. 2, 6th Ed. May2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e.g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e.g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol,propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones,e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers,e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas;products of vegetable origin, e.g. cereal meal, tree bark meal, woodmeal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemusifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols,or of fatty acid esters. Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates, and carboxylatedalcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinylpyrrolidone, vinyl-alcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B—C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxilaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), anorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons,polyvinylacetates, polyvinyl alcohols, polyacrylates, biological orsynthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)10-60 wt % of a compound I according to the invention and 5-15 wt %wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/orin a water-soluble solvent (e.g. alcohols) ad 100 wt %. The activesubstance dissolves upon dilution with water.ii) Dispersible concentrates (DC)5-25 wt % of a compound I according to the invention and 1-10 wt %dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent(e.g. cyclohexanone) ad 100 wt %. Dilution with water gives adispersion.iii) Emulsifiable concentrates (EC)15-70 wt % of a compound I according to the invention and 5-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in water-insoluble organic solvent (e.g.aromatic hydrocarbon) ad 100 wt %. Dilution with water gives anemulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I according to the invention and 1-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent(e.g. aromatic hydrocarbon). This mixture is introduced into water ad100 wt % by means of an emulsifying machine and made into a homogeneousemulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I according to theinvention are comminuted with addition of 2-10 wt % dispersants andwetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate),0.1-2 wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give afine active substance suspension. Dilution with water gives a stablesuspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.vi) Water-dispersible granules and water-soluble granules (WG, SG)50-80 wt % of a compound I according to the invention are ground finelywith addition of dispersants and wetting agents (e.g. sodiumlignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared aswater-dispersible or water-soluble granules by means of technicalappliances (e.g. extrusion, spray tower, fluidized bed). Dilution withwater gives a stable dispersion or solution of the active substance.vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)50-80 wt % of a compound I according to the invention are ground in arotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodiumlignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) andsolid carrier (e.g. silica gel) ad 100 wt %. Dilution with water gives astable dispersion or solution of the active substance.viii) Gel (GW, GF)In an agitated ball mill, 5-25 wt % of a compound I according to theinvention are comminuted with addition of 3-10 wt % dispersants (e.g.sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose)and water ad 100 wt % to give a fine suspension of the active substance.Dilution with water gives a stable suspension of the active substance.

iv) Microemulsion (ME)

5-20 wt % of a compound I according to the invention are added to 5-30wt % organic solvent blend (e.g. fatty acid dimethylamide andcyclohexanone), 10-25 wt % surfactant blend (e.g. alkohol ethoxylate andarylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1h to produce spontaneously a thermodynamically stable microemulsion.

iv) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I according to theinvention, 0-40 wt % water insoluble organic solvent (e.g. aromatichydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate,methacrylic acid and a di- or triacrylate) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). Radicalpolymerization initiated by a radical initiator results in the formationof poly(meth)acrylate microcapsules. Alternatively, an oil phasecomprising 5-50 wt % of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and anisocyanate monomer (e.g. diphenylmethene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e.g.polyvinyl alcohol). The addition of a polyamine (e.g.hexamethylenediamine) results in the formation of a polyureamicrocapsules. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.ix) Dustable powders (DP, DS)1-10 wt % of a compound I according to the invention are ground finelyand mixed intimately with solid carrier (e.g. finely divided kaolin) ad100 wt %.

x) Granules (GR, FG)

0.5-30 wt % of a compound I according to the invention is ground finelyand associated with solid carrier (e.g. silicate) ad 100 wt %.Granulation is achieved by extrusion, spray-drying or the fluidized bed.xi) Ultra-low volume liquids (UL)1-50 wt % of a compound I according to the invention are dissolved inorganic solvent (e.g. aromatic hydrocarbon) ad 100 wt %.

The compositions types i) to xi) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, and in particular between 0.5 and 75%,by weight of active substance. The active substances are employed in apurity of from 90% to 100%, preferably from 95% to 100% (according toNMR spectrum).

Solutions for seed treatment (LS), Suspoemulsions (SE), flowableconcentrates (FS), powders for dry treatment (DS), water-dispersiblepowders for slurry treatment (WS), water-soluble powders (SS), emulsions(ES), emulsifiable concentrates (EC) and gels (GF) are usually employedfor the purposes of treatment of plant propagation materials,particularly seeds. The compositions in question give, aftertwo-to-tenfold dilution, active substance concentrations of from 0.01 to60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-usepreparations. Application can be carried out before or during sowing.Methods for applying compound I and compositions thereof, respectively,on to plant propagation material, especially seeds include dressing,coating, pelleting, dusting, soaking and in-furrow application methodsof the propagation material. Preferably, compound I or the compositionsthereof, respectively, are applied on to the plant propagation materialby a method such that germination is not induced, e.g. by seed dressing,pelleting, coating and dusting.

When employed in plant protection, the amounts of active substancesapplied are, depending on the kind of effect desired, from 0.001 to 2 kgper ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e.g. bydusting, coating or drenching seed, amounts of active substance of from0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to100 g and most preferably from 5 to 100 g, per 100 kilogram of plantpropagation material (preferably seeds) are generally required. Whenused in the protection of materials or stored products, the amount ofactive substance applied depends on the kind of application area and onthe desired effect. Amounts customarily applied in the protection ofmaterials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of activesubstance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to the activesubstances or the compositions comprising them as premix or, ifappropriate not until immediately prior to use (tank mix). These agentscan be admixed with the compositions according to the invention in aweight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually froma predosage device, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank andfurther auxiliaries may be added, if appropriate. In a furtherembodiment, either individual components of the composition according tothe invention or partially premixed components, e.g. componentscomprising compounds I and/or active substances from the groups M) or F)(see below), may be mixed by the user in a spray tank and furtherauxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e. g.components comprising compounds I and/or active substances from thegroups M.1 to M.UN.X or F.I to F.XII, can be applied jointly (e.g. aftertank mix) or consecutively.

The following list M of pesticides, grouped according the Mode of ActionClassification of the Insecticide Resistance Action Committee (IRAC),together with which the compounds according to the invention can be usedand with which potential synergistic effects might be produced, isintended to illustrate the possible combinations, but not to impose anylimitation:

M.1 Acetylcholine esterase (AChE) inhibitors from the class ofM.1A carbamates, for example aldicarb, alanycarb, bendiocarb,benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb,isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb andtriazamate; or from the class ofM.1B organophosphates, for example acephate, azamethiphos,azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos,chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;M.2. GABA-gated chloride channel antagonists such as:M.2A cyclodiene organochlorine compounds, as for example endosulfan orchlordane; orM.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil,flufiprole, pyrafluprole and pyriprole;M.3 Sodium channel modulators from the class ofM.3A pyrethroids, for example acrinathrin, allethrin, d-cis-transallethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrinS-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zetacypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin,tau-fluvalinate, halfenprox, imiprothrin, meperfluthrin, metofluthrin,momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin,pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; orM.3B sodium channel modulators such as DDT or methoxychlor;M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class ofM.4A neonicotinoids, for example acteamiprid, chlothianidin,dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; orthe compoundsM.4A.1:1-[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,8-Epoxy-1H-imidazo[1,2-a]azepine;orM.4A.2:1-[(6-chloro-3-pyridyl)methyl]-2-nitro-1-[(E)-pentylideneamino]guanidine;orM4.A.3:1-[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahydro-2H-imidazo[1,2-a]pyridine;or M.4B nicotine.M.5 Nicotinic acetylcholine receptor allosteric activators from theclass of spinosyns, for example spinosad or spinetoram;M.6 Chloride channel activators from the class of avermectins andmilbemycins, for example abamectin, emamectin benzoate, ivermectin,lepimectin or milbemectin;M.7 Juvenile hormone mimics, such asM.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene;or others as M.7B fenoxycarb or M.7C pyriproxyfen;M.8 miscellaneous non-specific (multi-site) inhibitors, for exampleM.8A alkyl halides as methyl bromide and other alkyl halides, orM.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8Etartar emetic;M.9 Selective homopteran feeding blockers, for exampleM.9B pymetrozine, or M.9C flonicamid;M.10 Mite growth inhibitors, for exampleM.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;M.11 Microbial disruptors of insect midgut membranes, for examplebacillus thuringiensis or bacillus sphaericus and the insecticdalproteins they produce such as bacillus thuringiensis subsp. israelensis,bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillusthuringiensis subsp. kurstaki and bacillus thuringiensis subsp.tenebrionis, or the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab,mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;M.12 Inhibitors of mitochondrial ATP synthase, for exampleM.12A diafenthiuron, orM.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatinoxide, or M.12C propargite, or M.12D tetradifon;M.13 Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC or sulfluramid;M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, forexample nereistoxin analogues as bensultap, cartap hydrochloride,thiocyclam or thiosultap sodium;M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureasas for example bistrifluron, chlorfluazuron, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron or triflumuron;M.16 Inhibitors of the chitin biosynthesis type 1, as for examplebuprofezin;M.17 Moulting disruptors, Dipteran, as for example cyromazine;M.18 Ecdyson receptor agonists such as diacylhydrazines, for examplemethoxyfenozide, tebufenozide, halofenozide, fufenozide orchromafenozide;M.19 Octopamin receptor agonists, as for example amitraz;M.20 Mitochondrial complex III electron transport inhibitors, forexampleM.20A hydramethylnon, or M.20B acequinocyl, or M.20C fluacrypyrim;M.21 Mitochondrial complex I electron transport inhibitors, for exampleM.21A METI acaricides and insecticides such as fenazaquin,fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, orM.21B rotenone;M.22 Voltage-dependent sodium channel blockers, for exampleM.22A indoxacarb, or M.22B metaflumizone, or M.22C1-[(E)-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(difluoromethoxy)phenyl]urea;M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic andTetramic acid derivatives, for example spirodiclofen, spiromesifen orspirotetramat;M.24 Mitochondrial complex IV electron transport inhibitors, for exampleM.24A phosphine such as aluminium phosphide, calcium phosphide,phosphine or zinc phosphide, or M.24B cyanide.M.25 Mitochondrial complex II electron transport inhibitors, such asbeta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;M.28 Ryanodine receptor-modulators from the class of diamides, as forexample flubendiamide, chlorantraniliprole (Rynaxypyr®),cyantraniliprole (Cyazypyr®), or the phthalamide compoundsM.28.1:(R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamidandM.28.2:(S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,or the compoundM.28.3:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chlorpyridin-2-yl)-1H-pyrazole-5-carboxamide(proposed ISO name: cyclaniliprole), or the compoundM.28.4:methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate;or a compound selected from M.28.5a) to M.28.5l):M.28.5a)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5b)N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5c)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5d)N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5e)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide;M.28.5f)N-[4,6-dibromo-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5g)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5h)N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5i)N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-5-bromo-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide;M.28.5j)5-chloro-2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(1-cyano-1-methyl-ethyl)carbamoyl]phenyl]pyrazole-3-carboxamide;M.28.5k)5-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2-pyridyl)pyrazole-3-carboxamide;M.28.5l)N-[2-(tert-butylcarbamoyl)-4-chloro-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(fluoromethoxy)pyrazole-3-carboxamide;or a compound selected fromM.28.6N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)-3-iodo-phthalamide;orM.28.73-chloro-N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)phthalamide;M.UN.X insecticidal active compounds of unknown or uncertain mode ofaction, as for example azadirachtin, amidoflumet, benzoximate,bifenazate, bromopropylate, chinomethionat, cryolite, dicofol,flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonylbutoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, pyflubumide or thecompoundsM.UN.X.1:4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide,or the compoundM.UN.X.2: cyclopropaneacetic acid,1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]ester, or the compoundM.UN.X.3:11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,or the compoundM.UN.X.4:3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,or the compoundM.UN.X.5:1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,or actives on basis of bacillus firmus (Votivo, 1-1582); orM.UN.X.6; a compound selected from the group ofM.UN.X.6a)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide;M.UN.X.6b)(E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.UN.X.6c)(E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide;M.UN.X.6d)(E/Z)-N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.UN.X.6e)(E/Z)-N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.UN.X.6f)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoroacetamide;M.UN.X.6g)(E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoroacetamide;M.UN.X.6h)(E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamideandM.UN.X.6i)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoropropanamide.);or the compoundsM.UN.X.7:3-[3-chloro-5-(trifluoromethyl)phenyl]-4-oxo-1-(pyrimidin-5-ylmethyl)pyrido[1,2-a]pyrimidin-1-ium-2-olate;orM.UN.X.8:8-chloro-N-[2-chloro-5-methoxyphenyl)sulfonyl]-6-trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide;orM.UN.X.9:4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide;orM.UN.X.10:5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;orM.UN.X.11:4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide;orM.UN.X.12:4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide.

The commercially available compounds of the group M listed above may befound in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, BritishCrop Protection Council (2011) among other publications.

The quinoline derivative flometoquin is shown in WO2006/013896. Theaminofuranone compounds flupyradifurone is known from WO 2007/115644.The sulfoximine compound sulfoxaflor is known from WO2007/149134. Theacaricide pyflubumide is known from WO2007/020986. The isoxazolinecompounds have been described: M.UN.X.1 in WO2005/085216, M.UN.X.9 inWO2013/050317, M.UN.X.11 in WO2005/085216 and M.UN.X. in WO2009/002809and in WO2011/149749. The pyripyropene derivative M.UN.X.2 has beendescribed in WO 2006/129714. The spiroketal-substituted cyclic ketoenolderivative M.UN.X.3 is known from WO2006/089633 and thebiphenyl-substituted spirocyclic ketoenol derivative M.UN.X.4 fromWO2008/067911. Finally triazoylphenylsulfide like M.UN.X.5 have beendescribed in WO2006/043635 and biological control agents on basis ofbacillus firmus in WO2009/124707. The neonicotionids 4A.1 is known fromWO20120/069266 and WO2011/06946, the M.4.A.2 from WO2013/003977, theM4.A.3. from WO2010/069266.

The Metaflumizone analogue M.22C is described in CN 10171577. Thephthalamides M.28.1 and M.28.2 are both known from WO 2007/101540. Theanthranilamide M.28.3 has been described in WO2005/077934. The hydrazidecompound M.28.4 has been described in WO 2007/043677. Theanthranilamides M.28.5a) to M.28.5h) can be prepared as described in WO2007/006670, WO2013/024009 and WO2013/024010, the anthranilamideM.28.5i) is described in WO2011/085575, the M.28.5j) in WO2008/134969,the M.28.5k) in US2011/046186 and the M.28.5l) in WO2012/034403. Thediamide compounds M.28.6 and M.28.7 can be found in CN102613183.

The compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have beendescribed in WO2012/029672. The mesoionic antagonist compound M.UN.X.7was described in WO2012/092115, the nematicide M.UN.X.8 in WO2013/055584and the Pyridalyl-type analogue M.UN.X.10 in WO2010/060379.

Preferred additional pesticidally active ingredients are those selectedfrom the IRAC group 1, the Acetylcholinesterase (AChE) inhibitors,herein from the group 1A (Carbamtes) Thiodicarb, Methomyl and Carbaryl,and from the group 1B (Organophosphates), especially Acephate,Chlorpyriphos and Dimethoate, from the group 2B, the fiproles, hereespecially ethiprole and fipronil, from the group 3, the pyrethroids,here especially lambda-cyhalothrin, alpha-cypermethrin or deltametrin,and from the group 4A, the neonicotinoids, here especially acetamiprid,clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid orthiomethoxam.

Especially combinations of compounds of the invention with fiproles,neonictinoids or pyrethroids may possibly exhibit synergistic control ofstinkbugs (according to the Colby formula), in particular Euschistus,e.g. Euschistus heros.

The following list F of active substances, in conjunction with which thecompounds according to the invention can be used, is intended toillustrate the possible combinations but does not limit them:

F.I) Respiration Inhibitors

F.I-1) Inhibitors of complex III at Qo site:strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin,dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl,metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,pyrametostrobin, pyraoxystrobin, pyribencarb,triclopyricarb/chlorodincarb, trifloxystrobin,2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methylester and 2(2-(3-(2,6-dichlorophenyl)-1-methylallylideneaminooxymethyl)-phenyl)-2-methoxyimino-Nmethyl-acetamide; oxazolidinediones and imidazolinones: famoxadone,fenamidone;F.I-2) Inhibitors of complex II (e.g. carboxamides):carboxanilides: benodanil, benzovindiflupyr, bixafen, boscalid,carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr,isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad,sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4methyl-thiazole-5-carboxanilide, N-(3′,4′,5′ trifluorobiphenyl-2yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide (fluxapyroxad),N-(4′-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1Hpyrazole-4-carboxamide,N-(2-(1,3,3-trimethyl-butyl)phenyl)-1,3-dimethyl-5 fluoro-1H-pyrazole-4carboxamide,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide;F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom,[(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,[(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,[(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,[(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl2-methylpropanoate;F.I-4) Other respiration inhibitors (complex I, uncouplers)diflumetorim;(5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine;tecnazen; ametoctradin; silthiofam; nitrophenyl derivates: binapacryl,dinobuton, dinocap, fluazinam, ferimzone, nitrthal-isopropyl,and including organometal compounds: fentin salts, such asfentin-acetate, fentin chloride or fentin hydroxide;F.II) Sterol biosynthesis inhibitors (SBI fungicides)F.II-1) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles,imidazoles) triazoles: azaconazole, bitertanol, bromuconazole,cyproconazole, difenoconazole, diniconazole, diniconazole-M,epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol,hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil,paclobutrazole, penconazole, propiconazole, prothioconazole,simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol,triticonazole, uniconazole,1-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H[1,2,4]triazole,2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol;imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz,triflumizole; pyrimidines, pyridines and piperazines: fenarimol,nuarimol, pyrifenox, triforine,1-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H[1,2,4]triazole,2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol;F.II-2) Delta14-reductase inhitors (Amines, e.g. morpholines,piperidines) morpholines: aldimorph, dodemorph, dodemorph-acetate,fenpropimorph, tridemorph; piperidines: fenpropidin, piperalin;spiroketalamines: spiroxamine;F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;F.III) Nucleic acid synthesis inhibitorsF.III-1) RNA, DNA synthesisphenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M,kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;isoxazoles and iosothiazolones: hymexazole, octhilinone;F.III-2) DNA topisomerase inhibitors: oxolinic acid;F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase), hydroxy(2-amino)pyrimidines: bupirimate;F.IV) Inhibitors of cell division and or cytoskeletonF.IV-1) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl,carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;triazolopyrimidines: 5-chloro-7(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5a]pyrimidine;F.IV-2) Other cell division inhibitorsbenzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron,fluopicolide, zoxamide;F.IV-3) Actin inhibitors: benzophenones: metrafenone, pyriofenone;F.V) Inhibitors of amino acid and protein synthesisF.V-1) Methionine synthesis inhibitors (anilino-pyrimidines)anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;F.V-2) Protein synthesis inhibitors (anilino-pyrimidines) antibiotics:blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate,mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;F.VI) Signal transduction inhibitorsF.VI-1) MAP/Histidine kinase inhibitors (e.g. anilino-pyrimidines)dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;phenylpyrroles: fenpiclonil, fludioxonil;F.VI-2) G protein inhibitors: quinolines: quinoxyfen;F.VII) Lipid and membrane synthesis inhibitorsF.VII-1) Phospholipid biosynthesis inhibitors organophosphoruscompounds: edifenphos, iprobenfos, pyrazophos;dithiolanes: isoprothiolane;F.VII-2) Lipid peroxidation: aromatic hydrocarbons: dicloran,quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb,etridiazole;F.VII-3) Carboxyl acid amides (CAA fungicides)cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid,pyrimorph; valinamide carbamates: benthiavalicarb, iprovalicarb,pyribencarb, valifenalate andN-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamicacid-(4-fluorophenyl) ester;F.VII-4) Compounds affecting cell membrane permeability and fatty acids:1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,carbamates: propamocarb, propamocarb-hydrochlorid,F.VII-5) fatty acid amide hydrolase inhibitors:1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone;F.VIII) Inhibitors with Multi Site ActionF.VIII-1) Inorganic active substances: Bordeaux mixture, copper acetate,copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,methasulphocarb, metiram, propineb, thiram, zineb, ziram;F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides,chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet,dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene,pentachlorphenole and its salts, phthalide, tolylfluanid,N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;F.VIII-4) Guanidines and other: guanidine, dodine, dodine free base,guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate,iminoctadine-tris(albesilate),2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone;F.VIII-5) Ahtraquinones: dithianon;F.IX) Cell wall synthesis inhibitorsF.IX-1) Inhibitors of glucan synthesis: validamycin, polyoxin B;F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole,carpropamide, dicyclomet, fenoxanil;F.X) Plant defence inducersF.X-1) Salicylic acid pathway: acibenzolar-S-methyl;F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium;phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;F.XI) Unknown mode of action:bronopol, chinomethionat, cyflufenamid,cymoxanil, dazomet, debacarb, diclomezine, difenzoquat,difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover,flusulfamide, flutianil, methasulfocarb, nitrapyrin,nitrothal-isopropyl, oxathiapiprolin, oxin-copper, proquinazid,tebufloquin, tecloftalam, triazoxide,2-butoxy-6-iodo-3-propylchromen-4-one,N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenylacetamide,N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-Nmethyl formamidine, N′(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine,N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine, N′-(5-difluoromethyl-2methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine,2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)amide,2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide, methoxy-aceticacid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester andN-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide,3-[5-(4-chloro-phenyl)-2,3-dimethylisoxazolidin-3 yl]-pyridine,pyrisoxazole,5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1carbothioic acid S-allyl ester, N-(6-methoxy-pyridin-3-yl)cyclopropanecarboxylic acid amide, 5-chloro-1(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole,2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide,F.XII) Growth regulators: abscisic acid, amidochlor, ancymidol,6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequatchloride), choline chloride, cyclanilide, daminozide, dikegulac,dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol,fluthiacet, forchlorfenuron, gibberellic acid, inabenfide,indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquatchloride), naphthaleneacetic acid, N 6-benzyladenine, paclobutrazol,prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron,triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid,trinexapac-ethyl and uniconazole;F.XIII) Biological control agentsAmpelomyces quisquakis (e.g. AQ 10® from Intrachem Bio GmbH & Co. KG,Germany), Aspergillus flavus (e.g. AFLAGUARD® from Syngenta, CH),Aureobasidium pullulans (e.g. BOTECTOR® from bio-ferm GmbH, Germany),Bacillus pumilus (e.g. NRRL Accession No. B-30087 in SONATA® and BALLAD®Plus from AgraQuest Inc., USA), Bacillus subtilis (e.g. isolate NRRL-Nr.B-21661 in RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuestInc., USA), Bacillus subtilis var. amylaquefaciens FZB24 (e.g. TAEGRO®from Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (e.g.ASPIRE® from Ecogen Inc., USA), Candida saitoana (e.g. BIOCURE® (inmixture with lysozyme) and BIOCOAT® from Micro Flo Company, USA (BASFSE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., NZ),Clonostachys rosea f. catenulata, also named Gliocladium catenulatum(e.g. isolate J1446: PRESTOP® from Verdera, Finland), Coniothyriumminitans (e.g. CONTANS® from Prophyta, Germany), Cryphonectriaparasitica (e.g. Endothia parasitica from CNICM, France), Cryptococcusalbidus (e.g. YIELD PLUS® from Anchor Bio-Technologies, South Africa),Fusarium oxysporum (e.g. BIOFOX® from S.I.A.P.A., Italy, FUSACLEAN® fromNatural Plant Protection, France), Metschnikowia fructicola (e.g.SHEMER® from Agrogreen, Israel), Microdochium dimerum (e.g. ANTIBOT®from Agrauxine, France), Phlebiopsis gigantea (e.g. ROTSOP® fromVerdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX® from PlantProducts Co. Ltd., Canada), Pythium oligandrum DV74 (e.g. POLYVERSUM®from Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis(e.g. REGALIA® from Marrone Biolnnovations, USA), Talaromyces flavusV117b (e.g. PROTUS® from Prophyta, Germany), Trichoderma asperellumSKT-1 (e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd., Japan),T. atroviride LC52 (e.g. SENTINEL® from Agrimm Technologies Ltd, NZ), T.harzianum T-22 (e.g. PLANTSHIELD® der Firma BioWorks Inc., USA), T.harzianum TH 35 (e.g. ROOT PRO® from Mycontrol Ltd., Israel), T.harzianum T-39 (e.g. TRICHODEX® and TRICHODERMA 2000® from MycontrolLtd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride(e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012and T. viride ICC080 (e.g. REMEDIER® WP from Isagro Ricerca, Italy), T.polysporum and T. harzianum (e.g. BINAB® from BINAB Bio-Innovation AB,Sweden), T. stromaticum (e.g. TRICOVAB® from C.E.P.L.A.C., Brazil), T.virens GL-21 (e.g. SOILGARD® from Certis LLC, USA), T. viride (e.g.TRIECO® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIOCURE® F fromT. Stanes & Co. Ltd., Indien), T. viride TV1 (e.g. T. viride TV1 fromAgribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g. BOTRY-ZEN® fromBotry-Zen Ltd, NZ).

The commercially available compounds II of the group F listed above maybe found in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, BritishCrop Protection Council (2011) among other publications. Theirpreparation and their activity against harmful fungi is known (cf.:http://www.alanwood.net/pesticides/); these substances are commerciallyavailable. The compounds described by IUPAC nomenclature, theirpreparation and their fungicidal activity are also known (cf. Can. J.Plant Sci. 48(6), 587-94, 1968; EPA 141 317; EP-A 152 031; EP-A 226 917;EPA 243 970; EPA 256 503; EPA 428 941; EP-A 532 022; EP-A 1 028 125;EP-A 1 035 122; EPA 1 201 648; EPA 1 122 244, JP 2002316902; DE19650197; DE 10021412; DE 102005009458; U.S. Pat. No. 3,296,272; U.S.Pat. No. 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783;WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO06/87343; WO 07/82098; WO 07/90624, WO 11/028657).

The compounds of the invention may be mixed with soil, peat or otherrooting media for the protection of plants against seed-borne,soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions includepiperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in thecompositions will depend upon the intended target and the effectrequired.

An example of a rice selective herbicide which may be included ispropanil. An example of a plant growth regulator for use in cotton isPIX™.

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same

The invertebrate pest (also referred to as “animal pest”), i.e. theinsects, arachnids and nematodes, the plant, soil or water in which theplant is growing or may grow can be contacted with the compounds of thepresent invention or composition(s) comprising them by any applicationmethod known in the art. As such, “contacting” includes both directcontact (applying the compounds/compositions directly on theinvertebrate pest or plant—typically to the foliage, stem or roots ofthe plant) and indirect contact (applying the compounds/compositions tothe locus of the invertebrate pest or plant). The compounds of thepresent invention or the pesticidal compositions comprising them may beused to protect growing plants and crops from attack or infestation byanimal pests, especially insects, acaridae or arachnids by contactingthe plant/crop with a pesticidally effective amount of compounds of thepresent invention. The term “crop” refers both to growing and harvestedcrops.

The compounds of the present invention and the compositions comprisingthem are particularly important in the control of a multitude of insectson various cultivated plants, such as cereal, root crops, oil crops,vegetables, spices, ornamentals, for example seed of durum and otherwheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet andfield corn), soybeans, oil crops, crucifers, cotton, sunflowers,bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet,eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks,pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons,Brassica species, melons, beans, peas, garlic, onions, carrots, tuberousplants such as potatoes, sugar cane, tobacco, grapes, petunias,geranium/pelargoniums, pansies and impatiens.

The compounds of the present invention are employed as such or in formof compositions by treating the insects or the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms to beprotected from insecticidal attack with an insecticidally effectiveamount of the active compounds. The application can be carried out bothbefore and after the infection of the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms by theinsects.

Moreover, invertebrate pests may be controlled by contacting the targetpest, its food supply, habitat, breeding ground or its locus with apesticidally effective amount of compounds of the present invention. Assuch, the application may be carried out before or after the infectionof the locus, growing crops, or harvested crops by the pest.

The compounds of the present invention can also be applied preventivelyto places at which occurrence of the pests is expected.

The compounds of the present invention may be also used to protectgrowing plants from attack or infestation by pests by contacting theplant with a pesticidally effective amount of compounds of the presentinvention. As such, “contacting” includes both direct contact (applyingthe compounds/compositions directly on the pest and/or plant—typicallyto the foliage, stem or roots of the plant) and indirect contact(applying the compounds/compositions to the locus of the pest and/orplant).

“Locus” means a habitat, breeding ground, plant, seed, soil, area,material or environment in which a pest or parasite is growing or maygrow.

In general, “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

In the case of soil treatment or of application to the pests dwellingplace or nest, the quantity of active ingredient ranges from 0.0001 to500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, forexample, from 0.01 g to 1000 g of active compound per m² treatedmaterial, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95 weight %, preferably from 0.1 to 45weight %, and more preferably from 1 to 25 weight % of at least onerepellent and/or insecticide.

For use in treating crop plants, the rate of application of the activeingredients of this invention may be in the range of 0.1 g to 4000 g perhectare, desirably from 5 g to 500 g per hectare, more desirably from 5g to 200 g per hectare.

The compounds of the present invention are effective through bothcontact (via soil, glass, wall, bed net, carpet, plant parts or animalparts), and ingestion (bait, or plant part).

The compounds of the present invention may also be applied againstnon-crop insect pests, such as ants, termites, wasps, flies, mosquitos,crickets, or cockroaches. For use against said non-crop pests, compoundsof the present invention are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). Solid baits can be formed into various shapes and forms suitableto the respective application e.g. granules, blocks, sticks, disks.Liquid baits can be filled into various devices to ensure properapplication, e.g. open containers, spray devices, droplet sources, orevaporation sources. Gels can be based on aqueous or oily matrices andcan be formulated to particular necessities in terms of stickyness,moisture retention or aging characteristics. The bait employed in thecomposition is a product, which is sufficiently attractive to inciteinsects such as ants, termites, wasps, flies, mosquitos, crickets etc.or cockroaches to eat it. The attractiveness can be manipulated by usingfeeding stimulants or sex pheromones. Food stimulants are chosen, forexample, but not exclusively, from animal and/or plant proteins (meat-,fish- or blood meal, insect parts, egg yolk), from fats and oils ofanimal and/or plant origin, or mono-, oligo- or polyorganosaccharides,especially from sucrose, lactose, fructose, dextrose, glucose, starch,pectin or even molasses or honey. Fresh or decaying parts of fruits,crops, plants, animals, insects or specific parts thereof can also serveas a feeding stimulant. Sex pheromones are known to be more insectspecific. Specific pheromones are described in the literature and areknown to those skilled in the art.

For use in bait compositions, the typical content of active ingredientis from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to5% weight % of active ingredient.

Formulations of compounds of the present invention as aerosols (e.g inspray cans), oil sprays or pump sprays are highly suitable for thenon-professional user for controlling pests such as flies, fleas, ticks,mosquitos or cockroaches. Aerosol recipes are preferably composed of theactive compound, solvents such as lower alcohols (e.g. methanol,ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethylketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges ofapproximately 50 to 250° C., dimethylformamide, N-methylpyrrolidone,dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene,water, furthermore auxiliaries such as emulsifiers such as sorbitolmonooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fattyalcohol ethoxylate, perfume oils such as ethereal oils, esters of mediumfatty acids with lower alcohols, aromatic carbonyl compounds, ifappropriate stabilizers such as sodium benzoate, amphoteric surfactants,lower epoxides, triethyl orthoformate and, if required, propellants suchas propane, butane, nitrogen, compressed air, dimethyl ether, carbondioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

For use in spray compositions, the content of active ingredient is from0.001 to 80 weights %, preferably from 0.01 to 50 weight % and mostpreferably from 0.01 to 15 weight %.

The compounds of the present invention and its respective compositionscan also be used in mosquito and fumigating coils, smoke cartridges,vaporizer plates or long-term vaporizers and also in moth papers, mothpads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g.malaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis) with compounds of the present invention and itsrespective compositions also comprise treating surfaces of huts andhouses, air spraying and impregnation of curtains, tents, clothingitems, bed nets, tsetse-fly trap or the like. Insecticidal compositionsfor application to fibers, fabric, knitgoods, nonwovens, nettingmaterial or foils and tarpaulins preferably comprise a mixture includingthe insecticide, optionally a repellent and at least one binder.Suitable repellents for example are N,N-Diethyl-meta-toluamide (DEET),N,N-diethylphenylacetamide (DEPA),1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine,(2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexandiol,indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insectcontrol such as{(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate(Esbiothrin), a repellent derived from or identical with plant extractslike limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crudeplant extracts from plants like Eucalyptus maculata, Vitex rotundifolia,Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymbopogannartdus (citronella). Suitable binders are selected for example frompolymers and copolymers of vinyl esters of aliphatic acids (such as suchas vinyl acetate and vinyl versatate), acrylic and methacrylic esters ofalcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methylacrylate, mono- and di-ethylenically unsaturated hydrocarbons, such asstyrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dippingthe textile material into emulsions or dispersions of the insecticide orspraying them onto the nets. The compounds of the present invention andtheir compositions can be used for protecting wooden materials such astrees, board fences, sleepers, etc. and buildings such as houses,outhouses, factories, but also construction materials, furniture,leathers, fibers, vinyl articles, electric wires and cables etc. fromants and/or termites, and for controlling ants and termites from doingharm to crops or human being (e.g. when the pests invade into houses andpublic facilities). The compounds of the present invention are appliednot only to the surrounding soil surface or into the under-floor soil inorder to protect wooden materials but it can also be applied to lumberedarticles such as surfaces of the under-floor concrete, alcove posts,beams, plywoods, furniture, etc., wooden articles such as particleboards, half boards, etc. and vinyl articles such as coated electricwires, vinyl sheets, heat insulating material such as styrene foams,etc. In case of application against ants doing harm to crops or humanbeings, the ant controller of the present invention is applied to thecrops or the surrounding soil, or is directly applied to the nest ofants or the like.

The compounds of the present invention are also suitable for thetreatment of plant propagation material, especially seeds, in order toprotect them from insect pest, in particular from soil-living insectpests and the resulting plant's roots and shoots against soil pests andfoliar insects.

The compounds of the present invention are particularly useful for theprotection of the seed from soil pests and the resulting plant's rootsand shoots against soil pests and foliar insects. The protection of theresulting plant's roots and shoots is preferred. More preferred is theprotection of resulting plant's shoots from piercing and suckinginsects, wherein the protection from aphids is most preferred.

The present invention therefore comprises a method for the protection ofseeds from insects, in particular from soil insects and of theseedlings' roots and shoots from insects, in particular from soil andfoliar insects, said method comprising contacting the seeds beforesowing and/or after pregermination with a compound of the presentinvention, including a salt thereof. Particularly preferred is a method,wherein the plant's roots and shoots are protected, more preferably amethod, wherein the plants shoots are protected form piercing andsucking insects, most preferably a method, wherein the plants shoots areprotected from aphids.

The term seed embraces seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corms, bulbs,fruit, tubers, grains, cuttings, cut shoots and the like and means in apreferred embodiment true seeds.

The term seed treatment comprises all suitable seed treatment techniquesknown in the art, such as seed dressing, seed coating, seed dusting,seed soaking and seed pelleting.

The present invention also comprises seeds coated with or containing theactive compound.

The term “coated with and/or containing” generally signifies that theactive ingredient is for the most part on the surface of the propagationproduct at the time of application, although a greater or lesser part ofthe ingredient may penetrate into the propagation product, depending onthe method of application. When the said propagation product is(re)planted, it may absorb the active ingredient.

Suitable seed is seed of cereals, root crops, oil crops, vegetables,spices, ornamentals, for example seed of durum and other wheat, barley,oats, rye, maize (fodder maize and sugar maize/sweet and field corn),soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice,oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes,grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash,cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species,melons, beans, peas, garlic, onions, carrots, tuberous plants such aspotatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums,pansies and impatiens.

In addition, the active compound may also be used for the treatmentseeds from plants, which tolerate the action of herbicides or fungicidesor insecticides owing to breeding, including genetic engineeringmethods.

For example, the active compound can be employed in treatment of seedsfrom plants, which are resistant to herbicides from the group consistingof the sulfonylureas, imidazolinones, glufosinate-ammonium orglyphosate-isopropylammonium and analogous active substances (see forexample, EP-A 242 236, EP-A 242 246) (WO 92/00377) (EP-A 257 993, U.S.Pat. No. 5,013,659) or in transgenic crop plants, for example cotton,with the capability of producing Bacillus thuringiensis toxins (Bttoxins) which make the plants resistant to certain pests (EP-A 142 924,EP-A 193 259),

Furthermore, the active compound can be used also for the treatment ofseeds from plants, which have modified characteristics in comparisonwith existing plants consist, which can be generated for example bytraditional breeding methods and/or the generation of mutants, or byrecombinant procedures). For example, a number of cases have beendescribed of recombinant modifications of crop plants for the purpose ofmodifying the starch synthesized in the plants (e.g. WO 92/11376, WO92/14827, WO 91/19806) or of transgenic crop plants having a modifiedfatty acid composition (WO 91/13972).

The seed treatment application of the active compound is carried out byspraying or by dusting the seeds before sowing of the plants and beforeemergence of the plants.

Compositions which are especially useful for seed treatment are e.g.:

A Soluble concentrates (SL, LS)

D Emulsions (EW, EO, ES) E Suspensions (SC, OD, FS)

F Water-dispersible granules and water-soluble granules (WG, SG)G Water-dispersible powders and water-soluble powders (WP, SP, WS)

H Gel-Formulations (GF)

I Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, powders for dry treatment DS, waterdispersible powders for slurry treatment WS, water-soluble powders SSand emulsion ES and EC and gel formulation GF. These formulations can beapplied to the seed diluted or undiluted. Application to the seeds iscarried out before sowing, either directly on the seeds or after havingpregerminated the latter.

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/I Surfactant, 0 to 200 g/I antifreezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

Especially preferred FS formulations of compounds of the presentinvention for seed treatment usually comprise from 0.1 to 80% by weight(1 to 800 g/l) of the active ingredient, from 0.1 to 20% by weight (1 to200 g/l) of at least one surfactant, e.g. 0.05 to 5% by weight of awetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% byweight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% byweight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40%by weight, e.g. 1 to 40% by weight of a binder (sticker/adhesion agent),optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of athickener, optionally from 0.1 to 2% of an anti-foam agent, andoptionally a preservative such as a biocide, antioxidant or the like,e.g. in an amount from 0.01 to 1% by weight and a filler/vehicle up to100% by weight. Seed Treatment formulations may additionally alsocomprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials onthe seeds after treatment. Suitable binders are homo- and copolymersfrom alkylene oxides like ethylene oxide or propylene oxide,polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, andcopolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- andcopolymers, polyethyleneamines, polyethyleneamides andpolyethyleneimines, polysaccharides like celluloses, tylose and starch,polyolefin homo- and copolymers like olefin/maleic anhydride copolymers,polyurethanes, polyesters, polystyrene homo and copolymers.

Optionally, also colorants can be included in the formulation. Suitablecolorants or dyes for seed treatment formulations are Rhodamin B, C.I.Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigmentyellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigmentred 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigmentorange 34, pigment orange 5, pigment green 36, pigment green 7, pigmentwhite 6, pigment brown 25, basic violet 10, basic violet 49, acid red51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10,basic red 108.

Examples of a gelling agent is carrageen (Satiagel®)

In the treatment of seed, the application rates of the compounds of thepresent invention are generally from 0.01 g to 10 kg per 100 kg of seed,preferably from 0.05 g to 5 kg per 100 kg of seed, more preferably from0.1 g to 1000 g per 100 kg of seed and in particular from 0.1 g to 200 gper 100 kg of seed.

The invention therefore also relates to seed comprising a compound ofthe present invention, including an agriculturally useful salt of it, asdefined herein. The amount of the compound of the present invention,including an agriculturally useful salt thereof will in general varyfrom 0.01 g to 10 kg per 100 kg of seed, preferably from 0.05 g to 5 kgper 100 kg of seed, in particular from 0.1 g to 1000 g per 100 kg ofseed. For specific crops such as lettuce the rate can be higher.

Methods which can be employed for treating the seed are, in principle,all suitable seed treatment and especially seed dressing techniquesknown in the art, such as seed coating (e.g. seed pelleting), seeddusting and seed imbibition (e.g. seed soaking). Here, “seed treatment”refers to all methods that bring seeds and the compounds of the presentinvention into contact with each other, and “seed dressing” to methodsof seed treatment which provide the seeds with an amount of thecompounds of the present invention, i.e. which generate a seedcomprising a compound of the present invention. In principle, thetreatment can be applied to the seed at any time from the harvest of theseed to the sowing of the seed. The seed can be treated immediatelybefore, or during, the planting of the seed, for example using the“planter's box” method. However, the treatment may also be carried outseveral weeks or months, for example up to 12 months, before plantingthe seed, for example in the form of a seed dressing treatment, withouta substantially reduced efficacy being observed.

Expediently, the treatment is applied to unsown seed. As used herein,the term “unsown seed” is meant to include seed at any period from theharvest of the seed to the sowing of the seed in the ground for thepurpose of germination and growth of the plant.

Specifically, a procedure is followed in the treatment in which the seedis mixed, in a suitable device, for example a mixing device for solid orsolid/liquid mixing partners, with the desired amount of seed treatmentformulations, either as such or after previous dilution with water,until the composition is distributed uniformly on the seed. Ifappropriate, this is followed by a drying step.

The compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, are in particular alsosuitable for being used for combating parasites in and on animals.

An object of the present invention is therefore also to provide newmethods to control parasites in and on animals. Another object of theinvention is to provide safer pesticides for animals. Another object ofthe invention is further to provide pesticides for animals that may beused in lower doses than existing pesticides. And another object of theinvention is to provide pesticides for animals, which provide a longresidual control of the parasites.

The invention also relates to compositions comprising a parasiticidallyeffective amount of compounds of the present invention, including theirstereoisomers, veterinarily acceptable salts or N-oxides, and anacceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling,preventing and protecting animals against infestation and infection byparasites, which comprises orally, topically or parenterallyadministering or applying to the animals a parasiticidally effectiveamount of a compound of the present invention, including itsstereoisomers, veterinarily acceptable salts or N-oxides, or acomposition comprising it.

The invention also provides the use of a compound of the presentinvention, including its stereoisomers, veterinarily acceptable salts orN-oxides, for treating or protecting an animal from infestation orinfection by invertebrate pests.

The invention also provides a process for the preparation of acomposition for treating, controlling, preventing or protecting animalsagainst infestation or infection by parasites which comprises aparasiticidally effective amount of a compound of the present invention,including its stereoisomers, veterinarily acceptable salts or N-oxides,or a composition comprising it.

Activity of compounds against agricultural pests does not suggest theirsuitability for control of endo- and ectoparasites in and on animalswhich requires, for example, low, non-emetic dosages in the case of oralapplication, metabolic compatibility with the animal, low toxicity, anda safe handling.

Surprisingly it has now been found that compounds of formula (I) andtheir stereoisomers, veterinarily acceptable salts, tautomers andN-oxides, are suitable for combating endo- and ectoparasites in and onanimals.

The compounds of the present invention, especially compounds of formula(I) and their stereoisomers, veterinarily acceptable salts, tautomersand N-oxides, and compositions comprising them are preferably used forcontrolling and preventing infestations of and infections in animalsincluding warm-blooded animals (including humans) and fish. They are forexample suitable for controlling and preventing infestations andinfections in mammals such as cattle, sheep, swine, camels, deer,horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo,donkeys, fallow deer and reindeer, and also in furbearing animals suchas mink, chinchilla and raccoon, birds such as hens, geese, turkeys andducks and fish such as fresh- and salt-water fish such as trout, carpand eels. Compounds of the present invention, including theirstereoisomers, veterinarily acceptable salts or N-oxides, andcompositions comprising them are preferably used for controlling andpreventing infestations and infections in domestic animals, such as dogsor cats.

Infestations in warm-blooded animals and fish include, but are notlimited to, lice, biting lice, ticks, nasal bots, keds, biting flies,muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoesand fleas.

The compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, and compositions comprisingthem are suitable for systemic and/or non-systemic control of ecto-and/or endoparasites. They are active against all or some stages ofdevelopment.

The compounds of the present invention are especially useful forcombating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis,Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus,cockroaches (Blattaria—Blattodea), e.g. Blattella germanica, Blattellaasahinae, Periplaneta americana, Periplaneta japonica, Periplanetabrunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blattaorientalis,flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedesvexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians,Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anophelesleucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphoravicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria,Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyiahominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens,Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culisetainornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis,Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis,Glossina fuscipes, Glossina tachinoides, Haematobia irritans,Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconopstorrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoriapectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrusovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor,Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simuliumvittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanuslineola, and Tabanus similis,lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanuscorporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis,Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthusstramineus and Solenopotes capillatus.ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalussanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyommaamericanum, Ambryomma maculatum, Ornithodorus hermsi, Omithodorusturicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacotiand Dermanyssus gallinae,Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.,Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp.,Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptesspp.,Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduviussenilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Ariluscritatus,Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp.,Phtirus spp., and Solenopotes spp,Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenoponspp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp.,Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae(Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus,Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchuscontortus., Ostertagia spp., Cooperia spp., Nematodirus spp.,Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurusdentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamustrachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necatorspp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp.,Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylusabstrusus, and Dioctophyma renale,Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascarissuum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis(Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., andOxyuris equi,Camallanida, e.g. Dracunculus medinensis (guinea worm)Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocercaspp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophoraspp., Spirocerca lupi, and Habronema spp.,Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,Macracanthorhynchus hirudinaceus and Oncicola spp.,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimusspp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis,Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp.,and Nanocyetes spp.,Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidiumcaninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp.,Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp.,Anoplocephala spp., and Hymenolepis spp.

The present invention relates to the therapeutic and the non-therapeuticuse of compounds of the present invention and compositions comprisingthem for controlling and/or combating parasites in and/or on animals.The compounds of the present invention and compositions comprising themmay be used to protect the animals from attack or infestation byparasites by contacting them with a parasiticidally effective amount ofcompounds of the present invention and compositions containing them.

The compounds of the present invention and compositions comprising themcan be effective through both contact (via soil, glass, wall, bed net,carpet, blankets or animal parts) and ingestion (e.g. baits). As such,“contacting” includes both direct contact (applying the pesticidalmixtures/compositions containing the compounds of the present inventiondirectly on the parasite, which may include an indirect contact at itslocus-P, and optionally also administrating the pesticidalmixtures/composition directly on the animal to be protected) andindirect contact (applying the compounds/compositions to the locus ofthe parasite). The contact of the parasite through application to itslocus is an example of a non-therapeutic use of compounds of the presentinvention. “Locus-P” as used above means the habitat, food supply,breeding ground, area, material or environment in which a parasite isgrowing or may grow outside of the animal.

In general, “parasiticidally effective amount” means the amount ofactive ingredient needed to achieve an observable effect on growth,including the effects of necrosis, death, retardation, prevention, andremoval, destruction, or otherwise diminishing the occurrence andactivity of the target organism. The parasiticidally effective amountcan vary for the various compounds/compositions of the presentinvention. A parasiticidally effective amount of the compositions willalso vary according to the prevailing conditions such as desiredparasiticidal effect and duration, target species, mode of application,and the like.

The compounds of the present invention can also be applied preventivelyto places at which occurrence of the pests or parasites are expected.

Administration can be carried out both prophylactically andtherapeutically.

Administration of the active compounds is carried out directly or in theform of suitable preparations, orally, topically/dermally orparenterally.

The isothiazoline compounds of the present invention are lesspersistent, bioaccumulative and/or toxic than the compounds of the priorart, and especially the isoxazoline insecticides of the prior art, whichshow a high persistency in the soil and thus accumulate there.

EXAMPLES

The present invention is now illustrated in further details by thefollowing examples, without imposing any limitation thereto.

I. Preparation Examples

Compounds can be characterized e.g. by coupled High Performance LiquidChromatography/mass spectrometry (HPLC/MS), by ¹H-NMR and/or by theirmelting points.

Analytical HPLC Column:

Method A: Analytical UPLC column: Phenomenex Kinetex 1.7 μm XB-C18 100A;50×2.1 mm from Phenomenex, Germany. Elution: acetonitrile+0.1%trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA) in aratio from 5:95 to 100:0 in 1.5 min at 60° C. Flow: 0.8 mL/min to 1mL/min in 1.5 min. MS-method: ESI positive.

¹H-NMR: The signals are characterized by chemical shift (ppm, δ [delta])vs. tetramethylsilane, respectively CDCl₃ for ¹³C-NMR, by theirmultiplicity and by their integral (relative number of hydrogen atomsgiven). The following abbreviations are used to characterize themultiplicity of the signals: m=multiplett, q=quartett, t=triplett,d=doublet and s=singulett.

Abbreviations used are: h for hour(s), min for minute(s), r.t./roomtemperature for 20-25° C., THF for tetrahydrofuran, t-BuOH fortert-butanol, MTBE for methyl-tert-butylether, OAc for acetate, BuLi forn-butyl lithium, DMF for dimethyl formamide.

C.1 Compound Examples 1

Compound examples 1-1 to 1-16 correspond to compounds of formula C.1:

wherein R^(2a), R^(2b), R^(2c), R^(4b) and Y of each synthesizedcompound is defined in one row of table C.1 below.

The compounds were synthesized in analogy to Synthesis Example S.1 orS.2.

TABLE C.1 R^(2a), R^(2b), HPLC-MS: Method, R_(t) (min) & Ex. R^(2c)R^(4b) Y [M + H]⁺ or ¹H-NMR 1-1 Cl, Cl, Cl CH₃ OC(CH₃)₃ ¹H NMR (400 MHz,CDCl₃): δ 7.4 (m, 2H), 7.1 (s, 1H), 4.1 (d, 1H), 3.8 (d, 1H), 2.5 (s,3H), 1.6 (s, 9H). 1-2 Cl, Cl, Cl CH₃ OH ¹H NMR (400 MHz, d₆-DMSO): δ 7.8(s, 2H), 7.5 (s, 1H), 4.5 (d, 1H), 4.3 (d, 1H), 2.5 (s, 3H). 1-3 Cl, Cl,Cl CH₃ NHCH₂C(═O)—NHCH₂CF₃ A 1.416 613.7 1-4 Cl, Cl, Cl CH₃NHCH₂-(2-pyridyl) A 1.233 565.7 1-5 Cl, Cl, Cl CH₃ NHCH₂-(2-thiazolyl) A1.423 571.8 1-6 Cl, Cl, Cl CH₃ NHCH₂-(2-pyrimidinyl) A 1.397 566.7 1-7Cl, Cl, Cl CH₃ NHCH₂CF₃ A 1.531 557 1-8 Cl, Cl, Cl CH₃NH-(1,1-dioxo-thiethan-3-yl) ¹H NMR (400 MHz, d₆-DMSO): δ 8.9 (m, 1H),7.8 (s, 2H), 7.5 (s, 1H), 4.6- 4.5 (m, 4H), 4.4-4.2 (m, 3H), 2.5 (s,3H). 1-9 Cl, F, Cl CF₃ OH ¹H NMR (400 MHz, CDCl₃): δ 7.4 (s, 1H), 7.3(m, 2H), 4.2 (d, 1H), 3.85 (d, 1H). 1-10 Cl, F, Cl CF₃ NHCH₂-(2-pyridyl)A 1.264 602.2 1-11 Cl, F, Cl CF₃ NHCH₂C(═O)—NHCH₂CF₃ A 1.433 650.2 1-12Cl, F, Cl CF₃ NHCH₂-(2-pyrimidinyl) A 1.439 603.2 1-13 Cl, F, Cl CF₃NH-(1,1-dioxo-thiethan-3-yl) A 1.370 614.7 1-14 Cl, F, Cl CF₃NH-(3-thiethanyl) A 1.486 582.7 1-15 Cl, F, Cl CF₃ NHCH₂(cyclopropyl) A1.501 564.8 1-16 Cl, F, Cl CF₃ OCH₃ ¹H NMR (400 MHz, CDCl₃): δ 7.55 (s,1H), 7.4-7.35 (m, 2H), 4.2 (d, 1H), 3.95 (s, 3H), 3.85 (d, 1H).

Synthesis Example S.13-Methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide

(Compound example 1-7; compound of formula IA, wherein R^(2a), R^(2b)and R^(2c) are Cl, R^(4a) is H, R^(4b) is CH₃, and A isA²=—C(═O)NHCH₂CF₃)

Step 1: tert-Butyl 5-bromo-3-methyl-thiophene-2-carboxylate

To a solution of 5-bromo-3-methyl-thiophene-2-carboxylic acid (168 g,CAS 38239-45-1) and (Boc)₂O (250 g) in t-BuOH/THF (500 mL/500 mL) wasadded N,N-dimethyl-4-aminopyridine (“DMAP”, 10 g) and the mixture wasstirred overnight at 80° C. Then, the reaction was concentrated andwater (500 mL) was added. The aqueous layer was extracted with MTBE(2×500 mL). The combined organic layers were dried (Na₂SO₄), filteredand concentrated to give a residue which was purified by flashchromatography on silica gel to afford the title product (35 g, 17%).

¹H NMR (400 MHz, CDCl₃): δ 6.8 (s, 1H), 2.5 (s, 3H), 1.5 (s, 9H).

Step 2: tert-Butyl 5-formyl-3-methyl-thiophene-2-carboxylate

To a solution of the product of step 1 (28 g) in THF (300 mL) at −78° C.was added nBuLi (2.5 M in hexanes, 50 mL) dropwise, and the reaction wasstirred for 10 min at −78° C. 1-Formylpiperidine (18 g, CAS 2591-86-8)was added dropwise to the reaction, and the mixture was stirred foranother 30 min at −78° C. The reaction was quenched with water and theaqueous layer was extracted with MTBE. The organic layers were dried(Na₂SO₄), filtered and concentrated to give a residue which was purifiedby flash chromatography on silica gel (ethyl acetate/petroleum ether) toafford the title product (17 g, 74%).

Step 3: tert-Butyl 5-acetyl-3-methyl-thiophene-2-carboxylate

A solution of the product of step 2 (17 g) in THF (200 mL) at 0° C.under N₂ was treated with methyl magnesium bromide (27.5 mL, 2.9 Msolution in diethylether) over 15 min. The reaction was stirred at 0° C.for another 30 min. Then, a saturated aqueous NH₄Cl solution was addedand the aqueous layer was extracted with MTBE. The organic layer wasdried (Na₂SO₄), filtered and concentrated to afford the “crude alcohol”(20 g) which was used in the next step without any further purification.

The “crude alcohol” (20 g) in CH₂Cl₂ was treated with pyridiniumchlorochromate (“PCC”, 35.5 g) and stirred at r.t. overnight. Thereaction was filtered and the filtrate was concentrated to afford aresidue which was purified by flash chromatography on silica gel (ethylacetate/petroleum ether) to afford the title product (7 g, 40%).

Step 4: tert-Butyl3-methyl-5-[4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-2-enoyl]thiophene-2-carboxylate

A solution of the product of step 3 (7 g) in a mixture of DMF (30 mL)and THF (60 mL) was treated with2,2,2-trifluoro-1-(3,4,5-trichlorophenyl)ethanone (8.8 g, CAS158401-00-4). The reaction was stirred overnight at 70° C. using aDean-Stark apparatus to remove water. Then, the mixture was concentratedto give a residue which was purified by flash chromatography on silicagel (ethyl acetate/petroleum ether) to afford the title product (5.8 g,47%).

¹H NMR (400 MHz, CDCl₃): δ 7.45 (s, 1H), 7.4-7.2 (m, 3H), 2.5 (s, 3H),1.6 (s, 9H).

Step 5: tert-Butyl3-methyl-5-[4,4,4-trifluoro-3-sulfanyl-3-(3,4,5-trichlorophenyl)butanoyl]thiophene-2-carboxylate

The product of step 4 (5.8 g, mixture of E/Z-isomers) in CH₂Cl₂ (100 mL)was treated with triethylamine (II.7 g). At 0° C., gaseous hydrogensulfide (H₂S) was bubbled through the solution until the solution wassaturated. The mixture was stirred for another 1 h at 0° C., and thendiluted with CH₂Cl₂ (200 mL). The organic layer was washed with 10%aqueous hydrochloric acid solution (3×), dried (Na₂SO₄), filtered, andconcentrated to afford the crude product (5.9 g, quant.), which was usedin the next step without any further purification.

¹H NMR (400 MHz, CDCl₃): δ 7.7 (s, 2H), 7.5 (s, 1H), 4.1 (d, 1H), 3.8(d, 1H), 3.3 (s, 1H (SH)), 2.5 (s, 3H), 1.6 (s, 9H).

Step 6: tert-Butyl3-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]thiophene-2-carboxylate

At −15° C., the product of step 5 (5.9 g) in CH₂Cl₂ (100 mL) was treatedwith triethylamine (4.5 g) and with a solution ofhydroxylamine-O-sulfonic acid (“HOSA”, 1.5 g) in water (5 mL). Thereaction was warmed to 0° C. and stirred at 0° C. for 1 h, and thendiluted with CH₂Cl₂ (300 mL). The organic layer was washed withsaturated aqueous NH₄Cl solution (3×), dried (Na₂SO₄), and filtered. Tothe obtained solution, acid washed molecular sieves (AW 300, 150 g) wereadded and the mixture was stirred vigorously for 3 h at r.t. Then, themolecular sieves were filtered off over Celite, and the filtrateconcentrated to afford the product (4.7 g, 80%), which was used in thenext step without any further purification.

¹H NMR (400 MHz, CDCl₃): δ 7.4 (m, 2H), 7.1 (s, 1H), 4.1 (d, 1H), 3.8(d, 1H), 2.5 (s, 3H), 1.6 (s, 9H).

Step 7:3-Methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]thiophene-2-carboxylicacid

At 0° C., the product of step 6 (7.7 g) in CH₂Cl₂ (100 mL) was treatedwith trifluoroacetic acid (“TFA”, 50 mL), and the mixture stirredovernight at r.t. The reaction was concentrated, and co-evaporated withCH₂Cl₂ (5×) to afford the title product as a pale yellow solid (3.4 g,quant.) that was used in the next step without any further purification.

¹H NMR (400 MHz, d₆-DMSO): δ 7.8 (s, 2H), 7.5 (s, 1H), 4.5 (d, 1H), 4.3(d, 1H), 2.5 (s, 3H).

Step 8:3-Methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide

To a solution of the product of step 1 (0.3 g),2,2,2-trifluoroethylamine (0.08 g) and bromotripyrrolidinophosphoniumhexafluorophosphate (“PyBroP”, 0.35 g) in CH₂Cl₂ (40 mL) at r.t. wasadded N,N-diisopropylethylamine (0.26 g). The reaction was stirred atr.t. overnight, then concentrated to afford a residue that was purifiedby flash chromatography on silica gel (ethyl acetate/cyclohexane) toafford the title product (0.21 g, 60%).

HPLC-MS (method A): 1.531 min, M=557.0.

Synthesis Example S.25-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-(pyrimidin-2-ylmethyl)-3-(trifluoromethyl)thiophene-2-carboxamide

(Compound example 1-12; compound of formula IA, wherein R^(2a), andR^(2c) are Cl, R^(2b) is F, R^(4a) is H, R^(4b) is CF₃, and A isA²=—C(═O)NH-(pyrimidin-2-yl)

For the synthesis of methyl5-formyl-3-(trifluoromethyl)thiophene-2-carboxylate (CAS 189756-77-2),see US 2012/238569 (p. 34, paragraph [314]) or Helvetica Chimica Acta,1997, Vol. 80, 531-537.

Step 1: Methyl5-(1-hydroxyethyl)-3-(trifluoromethyl)-thiophene-2-carboxylate

To a solution of methyl5-formyl-3-(trifluoromethyl)-thiophene-2-carboxylate (8.5 g) in THF (370mL) at 0° C. was added a solution of methylmagnesium bromide (II.9 mL, 3M in diethylether) and the mixture was stirred at 0° C. for 1 h. Then,the reaction was quenched by the addition of saturated aqueous NH₄Clsolution (200 mL). The aqueous layer was extracted with ethyl acetate(2×100 mL). The combined organic layers were dried (Na₂SO₄), filteredand concentrated to give a residue which was purified by flashchromatography on silica gel (petroleum ether/ethyl acetate) to affordthe title product (6 g, 66%).

¹H NMR (400 MHz, CDCl₃): δ 7.19 (s, 1H), 5.15 (q, 1H), 3.92 (s, 3H),1.63 (d, 3H).

Step 2: Methyl 5-acetyl-3-(trifluoromethyl)-thiophene-2-carboxylate

To a solution of the product of step 1 (6 g) in CH₂Cl₂ (250 mL) at 0° C.was added Dess-Martin periodane (15 g, CAS 87413-09-0), and the reactionwas stirred at 0° C. overnight. Then, a mixture of aqueous solutions ofNa₂SO₃ and NaHCO₃ was added dropwise at 0° C. The aqueous layer wasextracted with CH₂Cl₂. The organic layers were combined, dried (Na₂SO₄),filtered and concentrated to give a residue which was purified by flashchromatography on silica gel (ethyl acetate/petroleum ether) to affordthe title product (3.5 g, 59%).

¹H NMR (400 MHz, CDCl₃): δ 7.82 (s, 1H), 3.97 (s, 3H), 2.62 (s, 3H).

Step 3: Methyl5-[3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-3-(trifluoromethyl)-thiophene-2-carboxylate

A solution of the product of step 2 (3.3 g) in a 1,2-dichloroethane(“DCE”, 100 mL) was treated with1-(3,5-dichloro-4-fluoro-phenyl)-2,2,2-trifluoro-ethanone (5.2 g, CAS1190865-44-1), K₂CO₃ (1.8 g), triethylamine (0.9 mL). The reaction wasstirred overnight at 100° C. Then, the mixture was diluted with waterand extracted with ethyl acetate. The organic layer was dried (Na₂SO₄),filtered and concentrated to give a residue which was purified by flashchromatography on silica gel (ethyl acetate/petroleum ether) to affordthe title product (2.4 g, 38%).

¹H NMR (400 MHz, CDCl₃): δ 8.19 (s, 1H), 7.78-7.72 (m, 1H), 7.47 (m,2H), 3.95 (s, 3H).

Step 4: Methyl5-[3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-sulfanyl-butanoyl]-3-(trifluoromethyl)-thiophene-2-carboxylate

The product of step 3 (2.31 g, mixture of E/Z-isomers) in CH₂Cl₂ (30 mL)was treated with N,N-diisopropylethylamine (3.6 g). At 0° C., gaseoushydrogen sulfide (H₂S) was bubbled through the solution until thesolution was saturated. The mixture was stirred for another 1 h at 0° C.Then, the pH was adjusted to pH 4-5 with aqueous 10% HCl solution) andthe mixture diluted with CH₂Cl₂ (200 mL). The organic layer was washedwith 10% aqueous HCl solution (1×) and water (2×), dried (Na₂SO₄),filtered, and concentrated to afford the crude product (2.4 g, 97%),which was used in the next step without any further purification.

¹H NMR (400 MHz, CDCl₃): δ 7.9 (s, 1H), 7.6 (m, 2H), 4.2 (d, 1H),4.0-3.8 (m, 4H), 3.2 (s, 1H (SH)).

Step 5: Methyl5-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-3-(trifluoromethyl)-thiophene-2-carboxylate(compound example 1-16)

At −10° C., the product of step 4 (2.4 g) in CH₂Cl₂ (30 mL) was treatedwith N,N-diisopropylethylamine (2.3 g) and with a solution ofhydroxylamine-O-sulfonic acid (“HOSA”, 0.62 g) in water (2 mL). Thereaction was warmed to 0° C. and stirred at 0° C. for 2 h, and thendiluted with CH₂Cl₂ (300 mL). The organic layer was washed withsaturated aqueous NH₄Cl solution (3×). Then, Na₂SO₄ andpara-toluenesulfonic acid (50 mg) were added, and the mixture wasstirred at r.t. for 1 h. Then, the reaction was filtered and the organiclayer was washed with 5% aqueous K₂CO₃ solution (2×), dried (Na₂SO₄),filtered, and concentrated to afford the crude product (2.24 g, 94%),which was used in the next step without any further purification.

¹H NMR (400 MHz, CDCl₃): δ 7.55 (s, 1H), 7.4-7.35 (m, 2H), 4.2 (d, 1H),3.95 (s, 3H), 3.85 (d, 1H).

Step 6:5-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-3-(trifluoromethyl)-thiophene-2-carboxylicacid (compound example 1-9)

At 0° C., the product of step 5 (2.2 g) in THF (60 mL) was treated witha solution of LiOH (0.6 g) in water (20 mL), and the mixture stirredovernight at r.t. Then, 10% aqueous HCl was added to adjust the pH ofthe reaction to pH 3-4. The aqueous layer was extracted with ethylacetate (3×). The organic layers were combined, washed with brine (1×),dried (Na₂SO₄), filtered, and concentrated. The obtained residue waspurified by trituration (petroleum ether/ethyl acetate 20:1) to affordthe product (3.9 g, 93%).

¹H NMR (400 MHz, CDCl₃): δ 7.4 (s, 1H), 7.3 (m, 2H), 4.2 (d, 1H), 3.85(d, 1H).

Step 7:5-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-(pyrimidin-2-ylmethyl)-3-(trifluoromethyl)-thiophene-2-carboxamide

To a solution of the product of step 6 (0.3 g),pyrimidin-2-ylmethanamine hydrochloride (0.1 g) andbromotripyrrolidinophosphonium hexafluorophosphate (“PyBroP”, 0.33 g) inCH₂Cl₂ (40 mL) at r.t. was added N,N-diisopropylethylamine (0.24 g). Thereaction was stirred at r.t. overnight. Then, water was added and thelayers separated. The organic layer was dried (Na₂SO₄), filtered andconcentrated to give a residue which was purified by flashchromatography on silica gel to afford the title product (0.14 g, 40%).

¹H NMR (400 MHz, CDCl₃): δ 8.8 (m, 2H), 7.7 (br. s, 1H), 7.4 (s, 1H),7.35 (m, 2H), 4.9 (m, 2H), 4.15 (d, 1H), 3.85 (d, 1H).

II. Evaluation of Pesticidal Activity

The activity of the compounds of formula I of the present invention canbe demonstrated and evaluated by the following biological test.

B.1 Diamond Back Moth (Plutella xylostella)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:aceteone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol). The test solution wasprepared at the day of use.

Leaves of cabbage were dipped in test solution and air-dried. Treatedleaves were placed in petri dishes lined with moist filter paper andinoculated with ten 3^(rd) instar larvae. Mortality was recorded 72hours after treatment. Feeding damages were also recorded using a scaleof 0-100%.

In this test, the compounds 1-3, 1-4, 1-5, 1-7, and 1-8 at 500 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.2 Green Peach Aphid (Myzus persicae)

For evaluating control of green peach aphid (Myzus persicae) throughsystemic means the test unit consisted of 96-well-microtiter platescontaining liquid artificial diet under an artificial membrane.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds werepipetted into the aphid diet, using a custom built pipetter, at tworeplications.

After application, 5-8 adult aphids were placed on the artificialmembrane inside the microtiter plate wells. The aphids were then allowedto suck on the treated aphid diet and incubated at about 23±1° C. andabout 50±5% relative humidity for 3 days. Aphid mortality and fecunditywas then visually assessed.

In this test, the compounds 1-3, 1-4, 1-10, 1-11, 1-12, 1-13, 1-14 and1-15 at 2500 ppm, respectively, showed a mortality of at least 75% incomparison with untreated controls.

B.3 Mediterranean Fruitfly (Ceratitis capitata)

For evaluating control of Mediterranean fruitfly (Ceratitis capitata)the test unit consisted of microtiter plates containing an insect dietand 50-80 C. capitata eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 5 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 28±1° C.and about 80±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-3, 1-7, 1-8, 1-10, 1-11, 1-12, 1-13, 1-14and 1-15 at 2500 ppm, respectively, showed a mortality of at least 75%in comparison with untreated controls.

B.4 Orchid Thrips (Dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay were obtained from acolony maintained continuously under laboratory conditions. For testingpurposes, the test compound is diluted in a 1:1 mixture of acetone:water(vol:vol), plus Kinetic HV at a rate of 0.01% v/v.

Thrips potency of each compound was evaluated by using afloral-immersion technique. All petals of individual, intact orchidflowers were dipped into treatment solution and allowed to dry in Petridishes. Treated petals were placed into individual resealable plasticalong with about 20 adult thrips. All test arenas were held undercontinuous light and a temperature of about 28° C. for duration of theassay. After 3 days, the numbers of live thrips were counted on eachpetal. The percent mortality was recorded 72 hours after treatment.

In this test, the compounds 1-3, and 1-8 at 500 ppm, respectively,showed a mortality of at least 75% in comparison with untreatedcontrols.

B.5 Southern Armyworm (Spodoptera eridania)

The active compounds were formulated by a Tecan liquid handler in 100%cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppmsolution was serially diluted in 100% cyclohexanone to make interimsolutions. These served as stock solutions for which final dilutionswere made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10 mlglass vials. A nonionic surfactant (Kinetic®) was included in thesolution at a volume of 0.01% (v/v). The vials were then inserted intoan automated electrostatic sprayer equipped with an atomizing nozzle forapplication to plants/insects.

Lima bean plants (variety Sieva) were grown 2 plants to a pot andselected for treatment at the 1^(st) true leaf stage. Test solutionswere sprayed onto the foliage by an automated electrostatic plantsprayer equipped with an atomizing spray nozzle. The plants were driedin the sprayer fume hood and then removed from the sprayer. Each pot wasplaced into perforated plastic bags with a zip closure. About 10 to 11armyworm larvae were placed into the bag and the bags zipped closed.Test plants were maintained in a growth room at about 25° C. and about20-40% relative humidity for 4 days, avoiding direct exposure tofluorescent light (24 hour photoperiod) to prevent trapping of heatinside the bags. Mortality and reduced feeding were assessed 4 daysafter treatment, compared to untreated control plants.

In this test, the compound 1-1 at 300 ppm showed a mortality of at least75% in comparison with untreated controls.

B.6 Vetch Aphid (Megoura viciae)

For evaluating control of vetch aphid (Megoura viciae) through contactor systemic means the test unit consisted of 24-well-microtiter platescontaining broad bean leaf disks.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the leaf disks at 2.5 μl, using a custom built microatomizer, at two replications. After application, the leaf disks wereair-dried and 5-8 adult aphids placed on the leaf disks inside themicrotiter plate wells. The aphids were then allowed to suck on thetreated leaf disks and incubated at about 23±1° C. and about 50±5%relative humidity for 5 days. Aphid mortality and fecundity was thenvisually assessed.

In this test, the compounds 1-5, 1-7, 1-10, 1-11, 1-12, 1-13, 1-14 and1-15 at 2500 ppm, respectively, showed a mortality of at least 75% incomparison with untreated controls.

B.7 Tobacco Budworm (Heliothis virescens)

For evaluating control of tobacco budworm (Heliothis virescens) the testunit consisted of 96-well-microtiter plates containing an insect dietand 15-25 H. virescens eggs. The compounds were formulated using asolution containing 75% v/v water and 25% v/v DMSO. Differentconcentrations of formulated compounds were sprayed onto the insect dietat 10 μl, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 28±1° C.and about 80±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-3, 1-4, 1-5, 1-7, 1-8, 1-9, 1-10, 1-11,1-12, 1-13, 1-14 and 1-15 at 2500 ppm, respectively, showed a mortalityof at least 75% in comparison with untreated controls.

B.8 Boll Weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomus grandis) the test unitconsisted of 96-well-microtiter plates containing an insect diet and5-10 A. grandis eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 5 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 25±1° C.and about 75±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10,1-11, 1-12, 1-13, 1-14 and 1-15 at 2500 ppm, respectively, showed amortality of at least 75% in comparison with untreated controls.

We claim:
 1. Isothiazoline compounds of the formula I

wherein X is a heterocyclic radical of formula II

wherein # is the attachment point to the remainder of the molecule; A isa group A¹, A², A³ or A⁴; wherein A¹ is selected from the groupconsisting of —C(═NR⁶)R⁸, —S(O)_(n)R⁹, —N(R⁵)R⁶ and —CN; A² is a groupof following formula:

wherein # denotes the bond to the aromatic ring of formula (I); W isselected from O and S; A³ is a group of following formula:

wherein # denotes the bond to the aromatic ring of formula (I); A⁴ is a3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated ormaximally unsaturated heteromonocyclic ring containing 1, 2, 3 or 4heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, or is a 8-, 9- or 10-membered saturated, partiallyunsaturated or maximally unsaturated heterobicyclic ring containing 1,2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, where the heteromonocyclic or heterobicyclicring is optionally substituted with one or more substituents R¹¹; G is Oor S; B¹, B² and B³ are each independently selected from the groupconsisting of N and CR², with the proviso that at most two of B¹, B² andB³ are N; R¹ is selected from the group consisting of C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyland —C(═O)OR¹⁵; each R² is independently selected from the groupconsisting of hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅,C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein thefour last mentioned aliphatic and cycloaliphatic radicals may bepartially or fully halogenated and/or may be substituted by one or moreradicals R⁸, —Si(R¹²)₃, —OR⁹, —S(O)_(n)R⁹, —NR^(10a)R^(10b), phenylwhich may be substituted by 1, 2, 3, 4 or 5 radicals R¹¹, and a 3-, 4-,5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated ormaximally unsaturated heteromonocyclic or heterobicyclic ring containing1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO,SO and SO₂, as ring members, where the heteromono- or heterobicyclicring may be substituted by one or more radicals R¹¹; R^(3a), R^(3b) areeach independently selected from the group consisting of hydrogen,halogen, hydroxyl, —CO₂R^(3d), C₁-C₃-alkyl, C₁-C₃-haloalkyl,C₂-C₃-alkenyl, C₂-C₃-alkynyl, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy,C₁-C₃-alkylthio, C₁-C₃-haloalkylthio, C₁-C₃-alkylsulfonyl andC₁-C₃-haloalkylsulfonyl; or R^(3a) and R^(3b) together form a group ═O,═C(R^(3c))₂, ═NOH or ═NOCH₃; each R^(3c) is independently selected fromthe group consisting of hydrogen, halogen, CH₃ and CF₃; R^(3d) isselected from the group consisting of hydrogen, C₁-C₆-alkyl andC₁-C₃-alkyloxy-C₁-C₃-alkyl-; R^(4a) and R^(4b) are independentlyselected from the group consisting of hydrogen, halogen, cyano, azido,nitro, —SCN, —SF₅, C₁-C₆-alkyl which may be partially or fullyhalogenated and/or may be substituted by one or more radicals R⁸,C₃-C₈-cycloalkyl which may be partially or fully halogenated and/or maybe substituted by one or more radicals R⁸, C₂-C₆-alkenyl which may bepartially or fully halogenated and/or may be substituted by one or moreradicals R⁸, C₂-C₆-alkynyl which may be partially or fully halogenatedand/or may be substituted by one or more radicals R⁸, —Si(R¹²)₃, —OR⁹,—S(O)_(n)R⁹, —NR^(10a)R^(10b), phenyl which may be substituted by 1, 2,3, 4 or 5 radicals R¹¹, and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-memberedsaturated, partially unsaturated or maximally unsaturatedheteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, where the heteromonocyclic or heterobicyclic ring maybe substituted by one or more radicals R¹¹; each R⁵ is independentlyselected from the group consisting of hydrogen, cyano, C₁-C₁₀-alkyl,C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the fourlast-mentioned aliphatic and cycloaliphatic radicals may be partially orfully halogenated and/or may be substituted with one or moresubstituents R⁸; and —S(O)_(n)R⁹, each R⁶ is independently selected fromthe group consisting of hydrogen, cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the four last-mentionedaliphatic and cycloaliphatic radicals may be partially or fullyhalogenated and/or may be substituted by one or more substituents R⁸,—OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹, —C(═O)NR^(10a)N(R^(10a))R^(10b),—Si(R¹²)₃, —C(═O)R⁸, —CH═NOR⁹, phenyl which may be substituted with 1,2, 3, 4, or 5 substituents R¹¹, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or10-membered saturated, partially unsaturated or maximally unsaturatedheteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4heteroatoms or heteroatom groups independently selected from N, O, S,NO, SO and SO₂, as ring members, where the heteromonocyclic orheterobicyclic ring may be substituted with one or more substituentsR¹¹; or R⁵ and R⁶, together with the nitrogen atom to which they arebound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partiallyunsaturated or maximally unsaturated heterocyclic ring, where the ringmay further contain 1, 2, 3 or 4 heteroatoms or heteroatom-containinggroups selected from O, S, N, SO, SO₂, C═O and C═S as ring members,wherein the heterocyclic ring may be substituted with 1, 2, 3, 4 or 5substituents independently selected from the group consisting ofhalogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, wherein thealiphatic or cycloaliphatic moieties in the twelve last-mentionedradicals may be substituted by one or more radicals R⁸, and phenyl whichmay be substituted with 1, 2, 3, 4 or 5 substituents R¹¹; or R⁵ and R⁶together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂, ═NR^(10a) or ═NOR⁹;R^(7a), R^(7b) are each independently selected from the group consistingof hydrogen, halogen, cyano, C₁-C₆-alkyl, C₃-C₈-cycloalkyl,C₂-C₆-alkenyl and C₂-C₆-alkynyl, wherein the four last-mentionedaliphatic and cycloaliphatic radicals may be partially or fullyhalogenated and/or may be substituted by one or more radicals R⁸; eachR⁸ is independently selected from the group consisting of cyano, azido,nitro, —SCN, —SF₅, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,C₃-C₈-cycloalkenyl, C₃-C₈-halocycloalkenyl, where the cycloaliphaticmoieties in the four last-mentioned radicals may be substituted by oneor more radicals R¹³; —Si(R¹²)₃, —OR⁹, —OSO₂R⁹, —S(O)_(n)R⁹,—N(R^(10a))R^(10b)), —C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b),—C(═O)OR⁹, —CH═NOR⁹, phenyl, optionally substituted with 1, 2, 3, 4 or 5substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated,partially unsaturated or maximally unsaturated heterocyclic ringcomprising 1, 2 or 3 heteroatoms or heteroatom groups selected from N,O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring isoptionally substituted with one or more substituents R¹⁶, or two R⁸present on the same carbon atom of an alkyl, alkenyl, alkynyl orcycloalkyl group together form a group ═O, ═C(R¹³)₂; ═S;═S(O)_(m)(R¹⁵)₂, ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR^(10a), ═NOR⁹; or═NN(R^(10a))R^(10b); or two radicals R⁸, together with the carbon atomsof an alkyl, alkenyl, alkynyl or cycloalkyl group which they are bondedto, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partiallyunsaturated carbocyclic or heterocyclic ring, where the heterocyclicring comprises 1, 2, 3 or 4 heteroatoms or heteroatom groupsindependently selected from N, O, S, NO, SO and SO₂, as ring members,and where the carbocyclic or heterocyclic ring is optionally substitutedwith one or more substituents R¹⁶; and R⁸ as a substituent on acycloalkyl ring is additionally selected from the group consisting ofC₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl and C₂-C₆-haloalkynyl, where the aliphatic moieties inthese six radicals may be substituted by one or more radicals R¹³; andR⁸ in the groups —C(═NR⁶)R⁸, —C(═O)R⁸ and ═C(R⁸)₂ is additionallyselected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl andC₂-C₆-haloalkynyl, where the aliphatic moieties in the sixlast-mentioned radicals may be substituted by one or more radicals R¹³;each R⁹ is independently selected from the group consisting of hydrogen,cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl-, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, where the aliphaticand cycloaliphatic moieties in the nine last-mentioned radicals may besubstituted by one or more radicals R¹³, —C₁-C₆-alkyl-C(═O)OR¹⁵,—C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),—C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),—C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), —Si(R¹²)₃, —S(O)_(n)R¹⁶,—S(O)_(n)N(R^(14a))R^(14b), —N(R^(10a))R^(10b), —N═C(R¹³)₂, —C(═O)R¹³,—C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), —C(═O)OR¹⁵, phenyl,optionally substituted with one or more substituents R¹⁶; and a 3-, 4-,5-, 6- or 7-membered saturated, partially unsaturated or maximallyunsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring is optionally substituted with oneor more substituents R¹⁶; and R⁹ in the groups —S(O)_(n)R⁹ and —OSO₂R⁹is additionally selected from the group consisting of C₁-C₆-alkoxy andC₁-C₆-haloalkoxy; R^(10a), R^(10b) are selected independently from oneanother from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, where the aliphaticand cycloaliphatic moieties in the eight last-mentioned radicals may besubstituted by one or more radicals R¹³; —C₁-C₆-alkyl-C(═O)OR¹⁵,—C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),—C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),—C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, —S(O)_(n)R¹⁶,—S(O)_(n)N(R^(14a))R^(14b), —C(═O)R¹³, —C(═O)OR¹⁵,—C(═O)N(R^(14a))R^(14b), —C(═S)R¹³, —C(═S)SR¹⁵, —C(═S)N(R^(14a))R^(14b),—C(═NR¹⁴)R¹³; phenyl, optionally substituted with 1, 2, 3, 4 or 5substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated,partially unsaturated or maximally unsaturated heterocyclic ringcomprising 1, 2, 3 or 4 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring isoptionally substituted with one or more substituents R¹⁶; or R^(19a) andR^(19b) form together with the nitrogen atom they are bonded to a 3-,4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring, wherein the heterocyclic ringmay additionally contain one or two heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring optionally carries one or more substituents selectedfrom halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a 3-, 4-, 5-, 6,or 7-membered saturated, partially unsaturated or maximally unsaturatedheterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring optionally carries one or more substituents R¹⁶; orR^(10a) and R^(10b) together form a group ═C(R¹³)₂, ═S(O)_(m)(R¹⁵)₂,═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR¹⁴ or ═NOR¹⁵; R¹¹ is independentlyselected from the group consisting of halogen, cyano, azido, nitro,—SCN, —SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic andcycloaliphatic radicals may be partially or fully halogenated and/or maybe substituted with one or more radicals R⁸, —OR⁹, —NR^(10a)R^(10b),—S(O)_(n)R⁹, —Si(R¹²)₃; phenyl, optionally substituted with 1, 2, 3, 4,or 5 substituents selected independently from R¹⁶; and a 3-, 4-, 5-, 6-or 7-membered saturated, partially unsaturated or maximally unsaturatedaromatic heterocyclic ring comprising 1, 2, 3 or 4 heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring is optionally substituted with oneor more substituents selected independently from R¹⁶; or two R¹¹ presenton the same ring carbon atom of an unsaturated or partially unsaturatedheterocyclic ring may together form a group ═O, ═C(R¹³)₂; ═S;═S(O)_(m)(R¹⁵)₂; ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR¹⁴, ═NOR¹⁵, or═NN(R^(14a))R^(14b); or two R¹¹ bound on adjacent ring atoms formtogether with the ring atoms to which they are bound a saturated 3-, 4-,5-, 6-, 7-, 8- or 9-membered ring, wherein the ring may contain 1 or 2heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴, NO, SO andSO₂ and/or 1 or 2 groups selected from C═O, C═S and C═NR¹⁴ as ringmembers, and wherein the ring may be substituted by one or more radicalsselected from the group consisting of halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring containing 1, 2 or 3 heteroatomsor heteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring may be substituted by one or moreradicals R¹⁶; each R¹² is independently selected from the groupconsisting of hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-haloalkoxy-C₁-C₆-alkyl, and phenyl, optionally substituted with 1,2, 3, 4, or 5 substituents R¹⁶; each R¹³ is independently selected fromthe group consisting of cyano, nitro, —OH, —SH, —SCN, —SF₅,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, —NR^(14a)R^(14b), trimethylsilyl,triethylsilyl, tert-butyldimethylsilyl, —C(═O)N(R^(14a))R^(14b),C₃-C₈-cycloalkyl which may be unsubstituted, partially or fullyhalogenated and/or may carry 1 or 2 radicals selected from cyano,C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo;phenyl, benzyl, phenoxy, where the phenyl moiety in the threelast-mentioned radicals may be unsubstituted or carry 1, 2, 3, 4 or 5substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated,partially unsaturated or maximally unsaturated heterocyclic ringcontaining 1, 2 or 3 heteroatoms or heteroatom groups selected from N,O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring maybe substituted by 1, 2 or 3 substituents R¹⁶; or two R¹³ present on thesame carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group maytogether be ═O, ═CH(C₁-C₄-alkyl), ═C(C₁-C₄-alkyl)C₁-C₄-alkyl, ═NR¹⁷ or═NOR¹⁷; and R¹³ as a substituent on a cycloalkyl ring is additionallyselected from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl andC₂-C₆-alkynyl, wherein the three last-mentioned aliphatic radicals maybe unsubstituted, partially or fully halogenated and/or may carry 1 or 2substituents selected from CN, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy and oxo; and R¹³ in the groups ═O(R¹³)₂, —N═C(R¹³)₂,—C(═O)R¹³, —C(═S)R¹³ and —C(═NR¹⁴)R¹³ is additionally selected from thegroup consisting of hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl andC₂-C₆-alkynyl, wherein the three last-mentioned aliphatic radicals maybe unsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from CN, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy and oxo; each R¹⁴ is independently selected from thegroup consisting of hydrogen, cyano, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,—C(═O)NR^(18a)R^(18b), trimethylsilyl, triethylsilyl,tert-butyldimethylsilyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,wherein the three last-mentioned aliphatic radicals may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituentsselected from halogen and cyano; and oxo; C₃-C₈-cycloalkyl which may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-alkylsulfonyl, C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyl-C₁-C₄-alkyl-,where the cycloalkyl moiety in the two last-mentioned radicals may besubstituted by 1 or 2 substituents selected from halogen and cyano; andoxo; phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties inthe four last-mentioned radicals may be unsubstituted and/or carry 1, 2,3 or 4 substituents selected from halogen, cyano, nitro, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, and(C₁-C₆-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated,partially unsaturated or maximally unsaturated heterocyclic ringcomprising 1, 2 or 3 heteroatoms or heteroatom groups selected from N,O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring isoptionally substituted with one or more substituents R¹⁶; R^(14a) andR^(14b), independently of each other, have one of the meanings given forR¹⁴; or R^(14a) and R^(14b), together with the nitrogen atom to whichthey are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partiallyunsaturated or maximally unsaturated heterocyclic ring, wherein theheterocyclic ring may additionally contain 1 or 2 heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring optionally carries one or moresubstituents selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; or R^(14a) and R¹⁴ or R^(14b) andR¹⁴, together with the nitrogen atoms to which they are bound in thegroup —C(═NR¹⁴)N(R^(14a))R^(14b), form a 3-, 4-, 5-, 6- or 7-memberedpartially unsaturated or maximally unsaturated heterocyclic ring,wherein the heterocyclic ring may additionally contain 1 or 2heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, where the heterocyclic ring optionally carries one ormore substituents selected from halogen, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy; each R¹⁵ is independently selected from the groupconsisting of hydrogen, cyano, trimethylsilyl, triethylsilyl,tert-butyldimethylsilyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,wherein the three last-mentioned aliphatic radicals may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl and oxo;C₃-C₈-cycloalkyl which may be unsubstituted, partially or fullyhalogenated and/or may carry 1 or 2 radicals selected from C₁-C₄-alkyl,C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl and oxo; phenyl, benzyl,pyridyl and phenoxy, wherein the four last-mentioned radicals may beunsubstituted, partially or fully halogenated and/or carry 1, 2 or 3substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy and (C₁-C₆-alkoxy)carbonyl; each R¹⁶ is independentlyselected from the group consisting of halogen, nitro, cyano, —OH, —SH,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)-aminocarbonyl,trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl; C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three last-mentioned aliphaticradicals may be unsubstituted, partially or fully halogenated and/or maycarry 1 or 2 radicals selected from cyano, C₃-C₄-cycloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo; C₃-C₈-cycloalkyl which may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from cyano, C₁-C₄-alkyl, C₃-C₄-cycloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo; phenyl, benzyl, pyridyl andphenoxy, wherein the four last mentioned radicals may be unsubstituted,partially or fully halogenated and/or carry 1, 2 or 3 substituentsselected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy and (C₁-C₆-alkoxy)carbonyl; or two R¹⁶ present togetheron the same atom of an unsaturated or partially unsaturated ring may be═O, ═S, ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═CH(C₁-C₄-alkyl) or═C(C₁-C₄-alkyl)C₁-C₄-alkyl; or two R¹⁶ on two adjacent carbon atoms formtogether with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or8-membered saturated, partially unsaturated or maximally unsaturatedring, wherein the ring may contain 1 or 2 heteroatoms or heteroatomgroups selected from N, O, S, NO, SO and SO₂, as ring members, andwherein the ring optionally carries one or more substituents selectedfrom halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; R¹⁷, R^(18a) and R^(18b), independently of each otherand independently of each occurrence, are selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,wherein the three last-mentioned aliphatic radicals may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,C₃-C₄-cycloalkyl which may be substituted by 1 or 2 substituentsselected from halogen and cyano; and oxo; C₃-C₈-cycloalkyl which may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl; phenyland benzyl; each n is independently 0, 1 or 2; and each m isindependently 0 or 1; and the N-oxides, stereoisomers and agriculturallyor veterinarily acceptable salts thereof.
 2. The compounds as claimed inclaim 1, where X is selected from heterocyclic radicals of formulaeII.1, II.2 and II.3

wherein # is the attachment point to the remainder of the molecule; andG, A, R^(4a) and R^(4b) are as defined in claim
 1. 3. The compounds asclaimed in claim 2, where X is the heterocyclic radical of formula II.1.4. The compounds as claimed in any of the preceding claims, where G isS.
 5. The compounds as claimed in any of the preceding claims, where Ais A¹ and A¹ is —CN.
 6. The compounds as claimed in any of claims 1 to4, where A is A¹ and A¹ is —C(═NR⁶)R⁸, where R⁸ is hydrogen and R⁶ is—NR^(10a)R^(10b); where R^(10a) is selected from hydrogen, C₁-C₆-alkyland C₁-C₆-haloalkyl; and R^(10b) is selected from—C(═O)N(R^(14a))R^(14b) and —C(═S)N(R^(14a))R^(14b); wherein R^(14a) isselected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; and R^(14b) isselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₆-alkylsubstituted with a CN group, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, phenylwhich is optionally substituted with 1, 2, 3 or 4, substituents eachindependently selected from the group consisting of halogen, cyano,nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyland C₂-C₄-haloalkynyl; and a heterocyclic ring selected from rings offormulae E-1 to E-54

wherein k is 0, 1, 2 or 3, n is 0, 1 or 2; and each R¹⁶ is independentlyselected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)aminocarbonyl; or two R¹⁶present on the same carbon atom of a saturated ring may form together ═Oor ═S.
 7. The compounds as claimed in any of claims 1 to 4, where A isA² and in A² W is O.
 8. The compounds as claimed in any of claims 1 and7, where in A² Y is H or —OR⁹, wherein R⁹ is selected from hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkyl substituted by one radicalR¹³, where R¹³ is preferably selected from CN, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl and a heterocyclic ring selected from rings offormulae E-1 to E-54 as defined in claim 6; and wherein R⁹ is inparticular hydrogen or C₁-C₆-alkyl.
 9. The compounds as claimed in anyof claims 1 and 7, where in A² Y is —N(R⁵)R⁶; wherein R⁵ and R⁶ are asdefined in claim
 1. 10. The compounds as claimed in claim 9, where R⁵selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN; and R⁶ isselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl whichcarries one radical R⁸, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituentsselected from F, CN and pyridyl; —N(R^(10a))R^(10b), wherein R^(10a) isselected from hydrogen and C₁-C₆-alkyl; and R^(10b) is selected fromhydrogen, —C(═O)N(R^(14a))R^(14b), phenyl, optionally substituted with1, 2, 3, 4 or 5 substituents R¹⁶, and a heterocyclic ring selected fromrings of formulae E-1 to E-54 as defined in claim 6; —CH═NOR⁹, whereinR⁹ is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; phenylwhich may be substituted with 1, 2, 3, 4, or 5 substituents R¹¹, and a3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximallyunsaturated heteromonocyclic ring containing 1, 2 or 3 heteroatoms orheteroatom groups independently selected from N, O, S, NO, SO and SO₂,as ring members, where the heteromonocyclic ring may be substituted withone or more substituents R¹¹; wherein each R¹¹ is independently selectedfrom the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl;or two R¹¹ present on the same carbon atom of a saturated heterocyclicring may form together ═O or ═S; each R⁸ is independently selected fromOH, CN, C₃-C₈-cycloalkyl which optionally carries a CN substituent,C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,—C(═O)N(R^(10a))R^(10b), phenyl, optionally substituted with 1, 2, 3, 4or 5 substituents R¹⁶, and a 3-, 4-, 5- or 6-membered saturated,partially unsaturated or maximally unsaturated heteromonocyclic ringcontaining 1, 2 or 3 heteroatoms or heteroatom groups independentlyselected from N, O, S, NO, SO and SO₂, as ring members, where theheteromonocyclic ring may be substituted with one or more substituentsR¹⁶; wherein R^(10a) is selected from the group consisting of hydrogen,C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN; R^(10b) is selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,CH₂—CN, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₃-C₆-cycloalkylmethyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, phenyl which isoptionally substituted with 1, 2, 3, 4 or 5 substituents selected fromthe group consisting of halogen, cyano, nitro, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio; and aheterocyclic ring selected from rings of formulae E-1 to E-54 as definedin claim 6; and each R¹⁶ as a substituent on phenyl or the heterocyclicrings is independently selected from the group consisting of halogen,cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or two R¹⁶present on the same carbon atom of a saturated heterocyclic ring mayform together ═O or ═S; or R⁵ and R⁶, together with the nitrogen atom towhich they are bound, form a 5- or 6-membered saturated heterocyclicring, where the ring may further contain 1 or 2 heteroatoms orheteroatom-containing groups selected from O, S, SO, SO₂, NH and C═O asring members, wherein the heterocyclic ring may be substituted with 1, 2or 3 substituents independently selected from the group consisting ofhalogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy andC₁-C₆-haloalkoxy; or R⁵ and R⁶ together form a group ═S(R⁹)₂, where R⁹is selected from C₁-C₆-alkyl and C₁-C₆-haloalkyl.
 11. The compounds asclaimed in claim 10, where R⁵ is hydrogen or C₁-C₃-alkyl; R⁶ is selectedfrom hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which carriesone radical R⁸, wherein R⁸ is as defined below; C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may besubstituted by 1 or 2 substituents selected from F, CN and pyridyl;—N(R^(10a))R^(10b), wherein R^(10a) is selected from hydrogen andC₁-C₆-alkyl and R^(10b) is selected from hydrogen,—C(═O)N(R^(14a))R^(14b), wherein R^(14a) is selected from the groupconsisting of hydrogen and C₁-C₆-alkyl and R^(14b) is selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₂-C₄-alkynyl, CH₂—CN,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy; phenyl, optionally substituted with 1, 2, 3, 4 or5 substituents R¹¹, wherein R¹¹ is as defined below; and aheteroaromatic ring selected from rings of formulae F-1 to F-42;—CH═NOR⁹, wherein R⁹ is selected from hydrogen, C₁-C₆-alkyl andC₁-C₆-haloalkyl; phenyl which may be substituted with 1, 2, 3, 4, or 5substituents R¹¹, wherein R¹¹ is as defined below; and aheteromonocyclic ring selected from rings of formulae F-1 to F-54

wherein k is 0, 1, 2 or 3, n is 0, 1 or 2, and each R¹¹ is independentlyselected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹¹present on the same carbon atom of a saturated heterocyclic ring mayform together ═O or ═S; R⁸ is selected from OH, CN, C₃-C₈-cycloalkylwhich optionally carries a CN substituent; C₃-C₈-halocycloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(10a))R^(10b), phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a heterocyclicring selected from rings of formulae E-1 to E-54 as defined in claim 6;wherein R^(10a) is selected from the group consisting of hydrogen andC₁-C₆-alkyl; R^(10b) is selected from the group consisting of hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, CH₂—CN, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; andeach R¹⁶ as a substituent on phenyl or heterocyclic rings of formulaeE-1 to E-54 is independently selected from the group consisting ofhalogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹⁶present on the same carbon atom of a saturated heterocyclic ring mayform together ═O or ═S.
 12. The compounds as claimed in any of claim 10or 11, where R⁵ is hydrogen; R⁶ is selected from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₄-alkyl which carries one radical R⁸,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl whichmay be substituted by 1 or 2 substituents selected from F and CN;—N(R^(10a))R^(10b), wherein R^(10a) is hydrogen and R^(10b) is—C(═O)N(R^(14a))R^(14b), wherein R^(14a) is selected from the groupconsisting of hydrogen and C₁-C₆-alkyl; and R^(14b) is selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, CH₂—CN,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; —CH═NOR⁹, wherein R⁹ is selected fromhydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; phenyl which may besubstituted with 1, 2, 3, 4, or 5 substituents R¹¹, and aheteromonocyclic ring selected from rings of formulae F-1 to F-54 asdefined in claim 11; wherein R⁸ is selected from CN, C₃-C₈-cycloalkylwhich optionally carries a CN substituent, C₃-C₈-halocycloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(10a))R^(10b), phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a heterocyclicring selected from rings of formulae E-1 to E-54 as defined in claim 6;wherein R^(10a) is selected from the group consisting of hydrogen andC₁-C₆-alkyl; R^(10b) is selected from the group consisting of hydrogen,C₁-C₆-alkyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, and R¹¹ andR¹⁶; independently of each occurrence and independently of each other,are selected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl,C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,aminocarbonyl, C₁-C₄-alkylaminocarbonyl anddi-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹¹ present on the same carbonatom of a saturated heterocyclic ring may form together ═O or ═S; or twoR¹⁶ present on the same carbon atom of a saturated heterocyclic ring mayform together ═O or ═S.
 13. The compounds as claimed in claim 12, whereR⁵ is hydrogen; R⁶ is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₄-alkyl which carries one radical R⁸, and a heteromonocyclic ringselected from rings of formulae F-1 to F-54, preferably F-43 to F-49,especially F-44, as defined in claim 11; wherein R⁸ is selected from CN,C₃-C₈-cycloalkyl which optionally carries a CN substituent,C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(10a))R^(10b),phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶,and a heterocyclic ring selected from rings of formulae E-1 to E-54,preferably E-1 to E-34, especially E-1 to E-3, E-7 and E-26 to E-31, asdefined in claim 6; wherein R^(10a) is selected from the groupconsisting of hydrogen and C₁-C₆-alkyl; R^(10b) is selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, and C₁-C₆-haloalkyl, and R¹¹and R¹⁶; independently of each occurrence and independently of eachother, are selected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl,C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,aminocarbonyl, C₁-C₄-alkylaminocarbonyl anddi-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹¹ present on the same carbonatom of a saturated heterocyclic ring may form together ═O or ═S; or twoR¹⁶ present on the same carbon atom of a saturated heterocyclic ring mayform together ═O or ═S.
 14. The compounds as claimed in any of claims 1to 4, where A is A³ and in A³ R^(7a) and R^(7b), independently of eachother, are selected from hydrogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl, andwhere preferably one of R^(7a) and R^(7b) is hydrogen and the other ishydrogen or methyl; R⁵ is selected from hydrogen, cyano, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the fourlast-mentioned aliphatic and cycloaliphatic radicals may be partially orfully halogenated and/or may be substituted with one or moresubstituents R⁸; and R⁶ is selected from hydrogen, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the fourlast-mentioned aliphatic and cycloaliphatic radicals may be partially orfully halogenated and/or may be substituted by one or more substituentsR⁸, —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹,—C(═O)NR^(10s)N(R^(10b))R^(10b), —C(═O)R⁸, and a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or maximally unsaturatedheteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4heteroatoms or heteroatom groups independently selected from N, O, S,NO, SO and SO₂, as ring members, where the heteromonocyclic orheterobicyclic ring may be substituted with one or more substituentsR¹¹; or R⁵ and R⁸, together with the nitrogen atom to which they arebound, form a 3-, 4-, 5- or 6-membered saturated, partially unsaturatedor maximally unsaturated heterocyclic ring, where the ring may furthercontain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groupsselected from O, S, N, SO, SO₂, C═O and C═S as ring members, wherein theheterocyclic ring may be substituted with 1, 2, 3, 4 or 5 substituentsindependently selected from the group consisting of halogen, cyano,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, wherein the aliphatic or cycloaliphatic moieties inthe twelve last-mentioned radicals may be substituted by one or moreradicals R⁸, and phenyl which may be substituted with 1, 2, 3, 4 or 5substituents R¹¹; or R⁵ and R⁶ together form a group ═C(R⁸)₂,═S(O)_(m)(R⁹)₂, ═NR^(10a) or ═NOR⁹; wherein m, n, R⁸, R⁹, R^(10a),R^(10b) and R¹¹ are as defined in claim
 1. 15. The compounds as claimedin claim 14, where R⁵ is selected from hydrogen, C₁-C₄-alkyl,C₂-C₃-alkynyl, —CH₂—CN and C₁-C₆-alkoxy-methyl and preferably fromhydrogen and C₁-C₄-alkyl; and R⁶ is —C(═O)R⁸; wherein R⁸ is as definedin claim
 1. 16. The compounds as claimed in claim 15, where R⁸ isselected from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₄-alkyl substituted by one radical R¹³,C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₃-C₈-cycloalkyl which optionally carries a CN substituent,C₃-C₈-halocycloalkyl, —N(R^(15a))R^(10b), —C(═O)N(R^(10a))R^(10b),—CH═NOR⁹, phenyl which is optionally substituted with 1, 2, 3, 4 or 5substituents R¹⁶; and a heterocyclic ring selected from rings offormulae E-1 to E-54 as defined in claim 6, wherein R⁹ is selected fromhydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; R^(10a) is selected fromhydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₃-C₆-cycloalkyl, andpreferably from hydrogen and C₁-C₄-alkyl; R^(10b) is selected fromhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl whichoptionally carries a CN substituent; —C(═O)N(R^(14a))R^(14b); phenyl,optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶; and aheteromonocyclic ring selected from rings of formulae E-1 to E-54 asdefined in claim 6; R¹³ is selected from CN, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(14a))R^(14b), phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶; and a heterocyclicring selected from rings of formulae E-1 to E-54 as defined in claim 6;R^(14a) is selected from hydrogen and C₁-C₆-alkyl; R^(14b) is selectedfrom hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, CH₂—CN, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₃-C₈-cycloalkyl, C₃-C₆-halocycloalkyl,C₃-C₆-cycloalkylmethyl-, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and each R¹⁶as a substituent on phenyl or heterocyclic rings of formulae E-1 to E-54is independently selected from the group consisting of halogen, cyano,nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹⁶present on the same carbon atom of a saturated heterocyclic ring mayform together ═O or ═S.
 17. The compounds as claimed in any of claims 1to 4, where A is A⁴ and A⁴ is selected from rings of formulae D-1 toD-173

wherein k is 0, 1, 2 or 3; n is 0, 1 or 2; and each R¹¹ is independentlyselected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹¹present on the same carbon atom of a saturated or partially unsaturatedring may form together ═O or ═S; and wherein A⁴ is preferably selectedfrom rings of formulae D-59, D-65 and D-66, and is in particular D-59.18. The compounds as claimed in any of the preceding claims, where B¹,B² and B³ are CR².
 19. The compounds as claimed in claim 18, where B¹ isCR², where R² is not hydrogen, and B² and B³ are CR², where R² isselected from hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅,C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein thefour last mentioned aliphatic and cycloaliphatic radicals may bepartially or fully halogenated and/or may be substituted by one or moreradicals R⁸; —OR⁹, —S(O)—R⁹ and —NR^(10a)R^(10b), wherein n, R⁸, R⁹,R^(10a) and R^(10b) are as defined in claim
 1. 20. The compounds asclaimed in claim 19, where R² is selected from hydrogen, halogen andC₁-C₂-haloalkyl, preferably from hydrogen, F, Cl, Br and CF₃.
 21. Thecompounds as claimed in any of the preceding claims, where R¹ isselected from C₁-C₄-haloalkyl and —C(═O)OR¹⁵, wherein R¹⁵ isC₁-C₄-alkyl, and where R¹ is preferably CF₃.
 22. The compounds asclaimed in any of the preceding claims, where R^(3a) and R^(3b) areselected, independently of each other, from hydrogen and halogen,preferably hydrogen and fluorine and are in particular hydrogen.
 23. Thecompounds as claimed in any of the preceding claims, where R^(4a) andR^(4b), independently of each other, selected from hydrogen, halogen,cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₅-cycloalkyl,C₃-C₅-halocycloalkyl, C₂-C₄-alkenyl, C₁-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio andC₁-C₄-haloalkylthio, and where in particular R^(4a) is hydrogen andR^(4b) is selected from hydrogen, methyl, trifluoromethyl, F, Cl and Br.24. An agricultural composition comprising at least one compound of theformula I, as defined in any of claims 1 to 23, a stereoisomer thereofand/or at least one agriculturally acceptable salt thereof, and at leastone inert liquid and/or solid agriculturally acceptable carrier.
 25. Aveterinary composition comprising at least one compound of the formulaI, as defined in any of claims 1 to 23, a stereoisomer thereof and/or atleast one veterinarily acceptable salt thereof, and at least one inertliquid and/or solid veterinarily acceptable carrier.
 26. The use of acompound as defined in any of claims 1 to 23, of a stereoisomer and/orof an agriculturally or veterinarily acceptable salt thereof forcombating invertebrate pests.
 27. The use of a compound as defined inany of claims 1 to 23, of a stereoisomer and/or of a veterinarilyacceptable salt thereof, for treating or protecting an animal frominfestation or infection by invertebrate pests.
 28. A method forcontrolling invertebrate pests which method comprises treating thepests, their food supply, their habitat or their breeding ground or aplant, plant propagation material, soil, area, material or environmentin which the pests are growing or may grow, or the materials, plants,plant propagation material, soils, surfaces or spaces to be protectedfrom invertebrate pest attack or infestation with a pesticidallyeffective amount of at least one imine compound of the formula I asdefined in any of claims 1 to 23, a stereoisomer thereof and/or at leastone agriculturally acceptable salt thereof.
 29. The method as claimed inclaim 28, for protecting plants from attack or infestation byinvertebrate pests, which method comprises treating the plants with apesticidally effective amount of at least one compound of the formula Ias defined in any of claims 1 to 23, a stereoisomer thereof and/or atleast one agriculturally acceptable salt thereof.
 30. The method asclaimed in claim 29, for protecting plant propagation material and/orthe plants which grow therefrom from attack or infestation byinvertebrate pests, which method comprises treating the plantpropagation material with a pesticidally effective amount of at leastone compound of the formula I as defined in any of claims 1 to 23, astereoisomer thereof and/or at least one agriculturally acceptable saltthereof.
 31. Plant propagation material, comprising at least onecompound of the formula I as defined in any of claims 1 to 23, astereoisomer thereof and/or at least one agriculturally acceptable saltthereof.
 32. A method for treating or protecting an animal frominfestation or infection by invertebrate pests which comprises bringingthe animal in contact with a pesticidally effective amount of at leastone compound of the formula I as defined in any of claims 1 to 23, astereoisomer thereof and/or at least one veterinarily acceptable saltthereof.